32159-21-0

Basic information

• Product Name: Z-PYR-OH
• Synonyms: n-cbz-l-pyroglutamicacidcrystalline;N-BENZYLOXYCARBONYL-L-PYROGLUTAMIC ACID;N-BENZYLOXYCARBONYL-L-PYRROLIDONE CARBOXYLIC ACID;N-CBZ-L-PYROGLUTAMIC ACID;N-ALPHA-CBZ-L-PYROGLUTAMIC ACID;N-ALPHA-CARBOBENZOXY-L-PYROGLUTAMIC ACID;(S)-5-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-BENZYL ESTER;Z-PGLU-OH
• CAS NO: 32159-21-0
• Molecular Formula: C₁₃H₁₃NO₅
• Molecular Weight: 263.25
• EINECS: 250-936-0
• Product Categories: pharmacetical;Pyroglutamic acid [Pyr, pGu];Unusual Amino Acids;Z-Amino acid series;Amino Acids;I - Z;Modified Amino Acids
• Mol File: 32159-21-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 128-130°C
• Boiling Point: 525.4 °C at 760 mmHg
• Flash Point: 271.5 °C
• Appearance: /
• Density: 1.408 g/cm³
• Vapor Pressure: 7.26E-12mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Sparingly)
• PKA: 3.03±0.20(Predicted)
• CAS DataBase Reference: Z-PYR-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-PYR-OH(32159-21-0)
• EPA Substance Registry System: Z-PYR-OH(32159-21-0)

Safety Data

• Statements: 22/22-36/37/38
• Safety Statements: 22-24/25-44-35-28-7-4
• WGK Germany: 3
• Hazardous Substances Data: 32159-21-0(Hazardous Substances Data)

Usage

Description

Z-PYR-OH, also known as Carbobenzyloxy-L-pyroglutamic acid, is an amino acid derivative that serves as a crucial building block in the synthesis of various compounds. It is characterized by its white powder form and is widely utilized in the pharmaceutical and chemical industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
Z-PYR-OH is used as an amino acid building block for the synthesis of various compounds, such as 5-Oxo-L-prolyl-L-proline (O859055). Its role in the creation of these compounds is essential for the development of new drugs and therapeutic agents.
Used in Chemical Industry:
In the chemical industry, Z-PYR-OH is utilized as a key component in the synthesis of complex molecules and organic compounds. Its unique properties make it a valuable asset in the development of new materials and chemical processes.
Used in Research and Development:
Z-PYR-OH is also employed in research and development settings, where it is used to study the properties and behavior of amino acid derivatives. This helps scientists and researchers gain a deeper understanding of the molecular structures and interactions that are crucial for the advancement of various scientific fields.

InChI:InChI=1/C13H13NO5/c15-11-7-6-10(12(16)17)14(11)13(18)19-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,16,17)/t10-/m0/s1

Synthetic route

sodium carbonate (497-19-8) + benzyl chloroformate (501-53-1) + L-Pyroglutamic acid (98-79-3) → Cbz-L-pGlu-OH (32159-21-0)

Conditions	Yield
In 1,4-dioxane; sodium hydroxide	87%

benzyl chloroformate (501-53-1) + L-Pyroglutamic acid (98-79-3) → Cbz-L-pGlu-OH (32159-21-0)

Conditions	Yield
With triethylamine In acetonitrile for 1h; Ambient temperature;	20%
With 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide; acetonitrile; methyloxirane 1.) r.t., 15 min, 2.) 1 h; Yield given. Multistep reaction;

N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) → Cbz-L-pGlu-OH (32159-21-0)

Conditions	Yield
With N-cyclohexyl-cyclohexanamine; dicyclohexyl-carbodiimide 1.) THF, 0 deg C; Multistep reaction;
Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: DCC / tetrahydrofuran / 0 °C 2: dicyclohexylamine (DCHA) / tetrahydrofuran / 0 °C View Scheme

N-(benzyloxycarbonyl)-L-glutamic acid anhydride (4124-76-9) → Cbz-L-pGlu-OH (32159-21-0)

Conditions	Yield
With N-cyclohexyl-cyclohexanamine In tetrahydrofuran at 0℃; Yield given;

2-bromothiophene (1003-09-4) + N-(benzyloxycarbonyl)-L-glutamic acid anhydride (4124-76-9) → (S)-4-Benzyloxycarbonylamino-5-oxo-5-thiophen-2-yl-pentanoic acid + N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) + Cbz-L-pGlu-OH (32159-21-0)

Conditions	Yield
Stage #1: 2-bromothiophene With magnesium In tetrahydrofuran at 40℃; for 2h; Stage #2: N-(benzyloxycarbonyl)-L-glutamic acid anhydride In tetrahydrofuran at -78℃; for 4h; Stage #3: With citric acid In tetrahydrofuran at -78 - 20℃; Title compound not separated from byproducts;

1-bromo-butane (109-65-9) + N-(benzyloxycarbonyl)-L-glutamic acid anhydride (4124-76-9) → (S)-4-Benzyloxycarbonylamino-5-oxo-nonanoic acid + N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) + Cbz-L-pGlu-OH (32159-21-0)

Conditions	Yield
Stage #1: 1-bromo-butane With magnesium In tetrahydrofuran at 40℃; for 2h; Stage #2: N-(benzyloxycarbonyl)-L-glutamic acid anhydride In tetrahydrofuran at -78℃; for 4h; Stage #3: With citric acid In tetrahydrofuran at -78 - 20℃; Title compound not separated from byproducts;

3-methoxyphenyl bromide (2398-37-0) + N-(benzyloxycarbonyl)-L-glutamic acid anhydride (4124-76-9) → (S)-4-Benzyloxycarbonylamino-5-(3-methoxy-phenyl)-5-oxo-pentanoic acid + N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) + Cbz-L-pGlu-OH (32159-21-0)

Conditions	Yield
Stage #1: 3-methoxyphenyl bromide With magnesium In tetrahydrofuran at 40℃; for 2h; Stage #2: N-(benzyloxycarbonyl)-L-glutamic acid anhydride In tetrahydrofuran at -78℃; for 4h; Stage #3: With citric acid In tetrahydrofuran at -78 - 20℃; Title compound not separated from byproducts;

1-bromo-hexane (111-25-1) + N-(benzyloxycarbonyl)-L-glutamic acid anhydride (4124-76-9) → (S)-4-Benzyloxycarbonylamino-5-oxo-undecanoic acid + N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) + Cbz-L-pGlu-OH (32159-21-0)

Conditions	Yield
Stage #1: 1-bromo-hexane With magnesium In tetrahydrofuran at 40℃; for 2h; Stage #2: N-(benzyloxycarbonyl)-L-glutamic acid anhydride In tetrahydrofuran at -78℃; for 4h; Stage #3: With citric acid In tetrahydrofuran at -78 - 20℃; Title compound not separated from byproducts;

phenylmagnesium chloride (100-59-4) + N-(benzyloxycarbonyl)-L-glutamic acid anhydride (4124-76-9) → (S)-4-Benzyloxycarbonylamino-5-oxo-5-phenyl-pentanoic acid + N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) + Cbz-L-pGlu-OH (32159-21-0)

Conditions	Yield
Stage #1: phenylmagnesium chloride; N-(benzyloxycarbonyl)-L-glutamic acid anhydride In tetrahydrofuran at -78℃; for 4h; Stage #2: With citric acid In tetrahydrofuran

phenyllithium (591-51-5) + N-(benzyloxycarbonyl)-L-glutamic acid anhydride (4124-76-9) → (S)-2-Benzyloxycarbonylamino-5-oxo-5-phenyl-pentanoic acid + (S)-4-Benzyloxycarbonylamino-5-oxo-5-phenyl-pentanoic acid + N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) + Cbz-L-pGlu-OH (32159-21-0)

Conditions	Yield
Stage #1: phenyllithium; N-(benzyloxycarbonyl)-L-glutamic acid anhydride In tetrahydrofuran at -78℃; for 4h; Stage #2: With citric acid In tetrahydrofuran

N-(benzyloxycarbonyl)-L-glutamic acid anhydride (4124-76-9) → N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) + Cbz-L-pGlu-OH (32159-21-0)

Conditions	Yield
Stage #1: N-(benzyloxycarbonyl)-L-glutamic acid anhydride With tert-butylmagnesium chloride In tetrahydrofuran at -78℃; for 4h; Stage #2: With citric acid In tetrahydrofuran
Stage #1: N-(benzyloxycarbonyl)-L-glutamic acid anhydride With phenylzinc chloride In tetrahydrofuran at -78℃; for 2h; Stage #2: With citric acid In tetrahydrofuran

N-(benzyloxycarbonyl)-L-glutamic acid anhydride (4124-76-9) + Ph3MgLi → (S)-2-Benzyloxycarbonylamino-5-oxo-5-phenyl-pentanoic acid + (S)-4-Benzyloxycarbonylamino-5-oxo-5-phenyl-pentanoic acid + N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) + Cbz-L-pGlu-OH (32159-21-0)

Conditions	Yield
Stage #1: N-(benzyloxycarbonyl)-L-glutamic acid anhydride; Ph3MgLi In tetrahydrofuran at -78 - 20℃; Stage #2: With citric acid In tetrahydrofuran

Cbz-L-pGlu-OH (32159-21-0) + methyl iodide (74-88-4) → (5S)-N-(benzyloxycarbonyl)-5-methoxycarbonyl-2-pyrrolidinone (75857-94-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane	98%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 6.5h; Heating / reflux;	98%

(2R,4'R,8'R)-α-tocopheramine (3398-70-7) + Cbz-L-pGlu-OH (32159-21-0) → vitamin E amine pyroglutamate conjugate + N-methylmorpholine hydrochloride (3651-67-0)

Conditions	Yield
Stage #1: Cbz-L-pGlu-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0 - 20℃; for 2h; Stage #2: (2R,4'R,8'R)-α-tocopheramine With triethylamine In tetrahydrofuran at 0℃;	A 98% B n/a

VESA-PEG-NH2 + Cbz-L-pGlu-OH (32159-21-0) → Reaxys ID: 11380187 + N-methylmorpholine hydrochloride (3651-67-0)

Conditions	Yield
Stage #1: Cbz-L-pGlu-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0 - 20℃; for 2h; Stage #2: VESA-PEG-NH2 With triethylamine In tetrahydrofuran; water at 0℃;	A 98% B n/a

tryptamine (61-54-1) + Cbz-L-pGlu-OH (32159-21-0) → (S)-2-[2-(1H-Indol-3-yl)-ethylcarbamoyl]-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester

Conditions	Yield
In tetrahydrofuran Heating;	90%

Cbz-L-pGlu-OH (32159-21-0) + benzyl chloride (100-44-7) → dibenzyl (2S)-5-oxotetrahydro-1H-pyrrole-1,2-dicarboxylate (71389-33-8)

Conditions	Yield
With triethylamine In acetone for 72h; Heating;	85%

Cbz-L-pGlu-OH (32159-21-0) → Z-Glp-NH2

Conditions	Yield
With pyridine; di-tert-butyl dicarbonate; ammonium bicarbonate In 1,4-dioxane 4-16 h;	84%

1,2,3-Benzotriazole (95-14-7) + Cbz-L-pGlu-OH (32159-21-0) → benzyl (2S)-2-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-5-oxotetrahydro-1H-pyrrole-1-carboxylate (958637-27-9)

Conditions	Yield
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In dichloromethane at 40 - 50℃; for 0.333333h; Stage #2: Cbz-L-pGlu-OH In dichloromethane at 20℃; for 2h; Further stages.;	84%

Cbz-L-pGlu-OH (32159-21-0) → tert-butyl N-benzyloxycarbonyl-L-pyroglutamate (81470-51-1)

Conditions	Yield
With perchloric acid In water at 20℃; for 16h;	79%

Cbz-L-pGlu-OH (32159-21-0) + N-methyl-m-toluidine (696-44-6) → benzyl (2S)-2-[methyl(m-tolyl)carbamoyl]-5-oxopyrrolidine-1-carboxylate

Conditions	Yield
With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃; for 12h;	75%

8-amino quinoline (578-66-5) + Cbz-L-pGlu-OH (32159-21-0) → C22H19N3O4

Conditions	Yield
Stage #1: Cbz-L-pGlu-OH With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0 - 20℃; for 1.5h; Stage #2: 8-amino quinoline In tetrahydrofuran at 20℃; for 6h;	74%

Cbz-L-pGlu-OH (32159-21-0) + 4-methoxy-aniline (104-94-9) → (S)-2-(4-Methoxy-phenylcarbamoyl)-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester (339994-37-5)

Conditions	Yield
With 4-methyl-morpholine; chloroformic acid ethyl ester In ethyl acetate at -15 - 20℃; for 50h;	68%

Cbz-L-pGlu-OH (32159-21-0) + Ala2-PheCH3, HBr (90427-75-1) → Z-Glp-Ala2-PheCH3 (88576-78-7)

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran	67%

Cbz-L-pGlu-OH (32159-21-0) + isobutene (115-11-7) → tert-butyl N-benzyloxycarbonyl-L-pyroglutamate (81470-51-1)

Conditions	Yield
With sulfuric acid In dichloromethane	67%
Stage #1: Cbz-L-pGlu-OH; isobutene With sulfuric acid In dichloromethane at 20℃; Cooling with ice; Stage #2: With sodium carbonate In dichloromethane; water	67%
With sulfuric acid In dichloromethane at 20℃; Cooling with ice;	67%
With sulfuric acid In dichloromethane at 20℃; Cooling with ice;	67%

Cbz-L-pGlu-OH (32159-21-0) + L-glutamic acid dibenzyl ester 4-toluenesulfonate (2791-84-6) → Z-pGlu-Glu(OBzl)-OBzl (122389-55-3)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane	63%

Cbz-L-pGlu-OH (32159-21-0) → benzyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate (153870-19-0)

Conditions	Yield
Stage #1: Cbz-L-pGlu-OH With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at -10℃; Stage #2: With sodium tetrahydroborate In methanol at 0℃;	61%
Multi-step reaction with 2 steps 1: N-methyl morpholine / tetrahydrofuran / 0.08 h / -5 °C 2: NaBH4 / tetrahydrofuran View Scheme

L-histidine methyl ester (95384-14-8) + Cbz-L-pGlu-OH (32159-21-0) → N-Z-L-pyroglutamyl-L-histidine methyl ester

Conditions	Yield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide; acetonitrile 1h at -10 deg C, then 12h at 4 deg C;	55%

Cbz-L-pGlu-OH (32159-21-0) + benzyl bromide (100-39-0) → dibenzyl (2S)-5-oxotetrahydro-1H-pyrrole-1,2-dicarboxylate (71389-33-8)

Conditions	Yield
With potassium hydrogencarbonate In N,N-dimethyl-formamide for 18h; Ambient temperature;	51%

Cbz-L-pGlu-OH (32159-21-0) + 3-chloro-benzenecarboperoxoic acid (937-14-4) → (R)-2-(3-Chloro-benzoyloxy)-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester (130654-55-6)

Conditions	Yield
With dicyclohexyl-carbodiimide In chloroform at 25℃; for 1h;	42%

Cbz-L-pGlu-OH (32159-21-0) + Ala3-PheCH3, HBr (90427-76-2) → Z-Glp-Ala3-PheCH3 (88576-80-1)

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran	40%

BOC-glycine (4530-20-5) + L-N-Boc-Ala (15761-38-3) + N-Boc-O-benzyl-L-threonine (15260-10-3) + Boc-Arg(Tos)-OH (13836-37-8) + BOC-O-benzyl-L-serine (23680-31-1) + Cbz-L-pGlu-OH (32159-21-0) + Boc-Asp(O-cyclohexyl)-OH (73821-95-1) + Boc-cysteine(4-Me-Bn) (61925-77-7) + Boc-(S)-Lys(2-Cl-Z)-OH (54613-99-9) + Nα-tert-butoxycarbonyl-1-formyl-L-tryptophan (47355-10-2) + N(α)-t-butoxycarbonyl-N(ϖ)-benzyloxymethyl-L-histidine (83468-83-1) → rerdused μ-conotoxin SIIIA

Conditions

Yield

Stage #1: Boc-cysteine(4-Me-Bn) With benzotriazol-1-ol In 1-methyl-pyrrolidin-2-one Automated synthesizer; Stage #2: With trifluoroacetic acid Stage #3: BOC-glycine; L-N-Boc-Ala; N-Boc-O-benzyl-L-threonine; Boc-Arg(Tos)-OH; BOC-O-benzyl-L-serine; Cbz-L-pGlu-OH; Boc-Asp(O-cyclohexyl)-OH; Boc-cysteine(4-Me-Bn); Boc-(S)-Lys(2-Cl-Z)-OH; Nα-tert-butoxycarbonyl-1-formyl-L-tryptophan; N(α)-t-butoxycarbonyl-N(ϖ)-benzyloxymethyl-L-histidine

22%

...Expand

Cbz-L-pGlu-OH (32159-21-0) → N-benzyloxycarbonyl-L-glutamic acid-5-hydrazide (4510-09-2)

Conditions	Yield
With hydrazine hydrate

Cbz-L-pGlu-OH (32159-21-0) + benzylamine (100-46-9) → N'-benzyl-N-benzyloxycarbonyl-L-glutamine (64153-27-1)

acetic acid tert-butyl ester (540-88-5) + Cbz-L-pGlu-OH (32159-21-0) → tert-butyl N-benzyloxycarbonyl-L-pyroglutamate (81470-51-1)

Conditions	Yield
With perchloric acid Yield given. Multistep reaction;
With perchloric acid Ambient temperature; Yield given;

diethyl 1-aminoethylphosphonate (54788-35-1) + Cbz-L-pGlu-OH (32159-21-0) → (S)-2-[1-(Diethoxy-phosphoryl)-ethylcarbamoyl]-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6.5h;

Cbz-L-pGlu-OH (32159-21-0) + L-tryptophan ethyl ester hydrochloride (2899-28-7, 6519-67-1, 61535-49-7, 67557-18-0, 68401-14-9) → N-carbobenzoxy-L-pyroglutamyl-L-tryptophan ethyl ester (87694-59-5)

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine 1.) THF, 0 deg C, 30 min, 2.) r.t., 3 h; Yield given. Multistep reaction;

Cbz-L-pGlu-OH (32159-21-0) + tert.-butyloxycarbonylalanyl-Nε-benzyloxycarbonyllysyl-serine methyl ester (84983-67-5) → Z-Pyr-Ala-Lys(Z)-Ser-OMe (84983-68-6)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; methoxybenzene; trifluoroacetic acid 1.) room temperature, 20 min 2.) DMF, 0 deg C, overnight, 4 deg C; Yield given. Multistep reaction;

Cbz-L-pGlu-OH (32159-21-0) + HCl.H-Leu-Gly-NH2 (38173-66-9) → (Z)--Leu-Gly-NH2 (39705-62-9)

Conditions	Yield
With 4-methyl-morpholine; triethylamine; isobutyl chloroformate 1.) THF, -20 deg C, 10 min, 2.) THF, DMF, H2O, RT, 1 h; Yield given. Multistep reaction;

Upstream product

• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 1003-09-4 2-bromothiophene 
• 4124-76-9 N-(benzyloxycarbonyl)-L-glutamic acid anhydride 
• 109-65-9 1-bromo-butane 
• 2398-37-0 3-methoxyphenyl bromide 
• 111-25-1 1-bromo-hexane 
• 100-59-4 phenylmagnesium chloride 
• 591-51-5 phenyllithium 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 501-53-1 benzyl chloroformate 
• 56-86-0 L-glutamic acid 
• 497-19-8 sodium carbonate 
• 98-79-3 L-Pyroglutamic acid 

Downstream Products

• 81470-51-1 tert-butyl N-benzyloxycarbonyl-L-pyroglutamate 
• 82379-40-6 (S)-2-Ethoxycarbonyloxycarbonyl-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester 
• 153870-19-0 benzyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate 
• 339994-37-5 (S)-2-(4-Methoxy-phenylcarbamoyl)-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester 
• 33208-87-6 C₂₃H₂₈N₆O₄ 
• 3651-67-0 N-methylmorpholine hydrochloride 
• 1033713-89-1 1-benzyl 2-tert-butyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate 
• 1033714-55-4 1-benzyl 2-tert-butyl (2S,5R)-5-methylpyrrolidine-1,2-dicarboxylate 
• 1199792-95-4 1-benzyl 2-tert-butyl (2S,5R)-5-ethylpyrrolidine-1,2-dicarboxylate 
• 1033709-61-3 tert-butyl (5R)-1-{[(5R,6S)-5,6-bis(4-chlorophenyl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-5-methyl-L-prolinate 
• 1443977-81-8 tert-butyl (5R)-1-{[(5R,6S)-5,6-bis(4-chlorophenyl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-5-ethyl-L-prolinate 
• 1033709-62-4 (5R)-1-{[(5R,6S)-5,6-bis(4-chlorophenyl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-5-methyl-L-proline 
• 1033709-22-6 (5R)-1-{[(5R,6S)-5,6-bis(4-chlorophenyl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-5-ethyl-L-proline 
• 1033714-59-8 (5R)-1-[(benzyloxy)carbonyl]-5-methyl-L-proline 

Relevant articles and documents

Selective Electrochemical Oxidation of Functionalized Pyrrolidines

A method for the selective electrochemical aminoxyl-mediated Shono-type oxidation of pyrrolidines to pyrrolidinones is described. These transformations show the high selectivity and functional group compatibility. This chemistry also demonstrates the use of an operationally simple ElectraSyn 2.0 and cost-effective stainless-steel electrode for the electrochemical oxidation of functionalized pyrrolidines.

Regioselective opening of N-Cbz glutamic and aspartic anhydrides with carbon nucleophiles

Depending on the experimental conditions, aspartic and glutamic anhydrides can be opened regioselectively with Grignard reagents, thus giving access to different isomers of chiral amino-ketoesters.

Synthesis, characterization and in vitro hydrolysis of L-pyroglutamyl-L-tryptophan derivatives as potential drug carriers

The condensation reaction of L-tryptophan with L-pyroglutamic acid or its N-carbobenzyloxy derivative in the presence of dicyclohexylcarbodiimide (DCC) afforded dipeptide molecules identified as L-pyroglutamyl-L-tryptophan derivatives. The synthesized dipeptide molecules offer a potentially useful means to obtain drug carriers and improve the poor uptake of drug molecules to the brain. The chemical hydrolysis characteristics in simulated gastro-intestinal juices are reported. No significant hydrolysis was observed.