(4R)-3-(tert-Butoxycarbonyl)-1,3-thiazolane-4-carboxylic acid

Base Information

• Chemical Name: (4R)-3-(tert-Butoxycarbonyl)-1,3-thiazolane-4-carboxylic acid
• CAS No.: 51077-16-8
• Molecular Formula: C9H15NO4S
• Molecular Weight: 233.288
• Hs Code.: 29341000
• DSSTox Substance ID: DTXSID60350896
• Nikkaji Number: J1.125.826C
• Wikidata: Q82126976
• Mol file: 51077-16-8.mol

Synonyms:51077-16-8;Boc-Thz-OH;(4R)-3-(tert-Butoxycarbonyl)-1,3-thiazolane-4-carboxylic acid;N-Boc-(R)-Thiazolidine-4-Carboxylic Acid;(r)-3-(tert-butoxycarbonyl)thiazolidine-4-carboxylic acid;(4R)-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-thiazolidine-4-carboxylic acid;(4R)-3-(tert-butoxycarbonyl)-1,3-thiazolidine-4-carboxylic acid;(4R)-3-[(tert-butoxy)carbonyl]-1,3-thiazolidine-4-carboxylic acid;boc-thioproline;n-boc-thioproline;Boc-Thiopro-OH;MFCD00077002;AO-710/25079001;SCHEMBL1022969;DTXSID60350896;FJWNZTPXVSWUKF-LURJTMIESA-N;(4R)-3-(tert-Butoxycarbonyl)-1,3-thiazolane-4-carboxylicacid;CCG-42064;AKOS010385802;CS-W012929;PS-6019;Boc-(R)-thiazolidine-4-carboxylic acid;BP-12389;TS-00634;D78198;EN300-248366;N-Boc-(R)-(-)-thiazolidine-4-carboxylic acid;A828430;SR-01000632095-1;(4R)-3-t-butoxycarbonylthiazolidine-4-carboxylic acid;Z756454262;(4R)-3-(tert-Butyloxycarbonyl)thiazolidine-4-carboxylic acid;(R)-3-tert-butoxycarbonyl-1,3-thiazolidine-4-carboxylic acid;N-tert-butoxycarbonyl-(R)-(-) thiazolidine-4-carboxylic acid;N-tert-butoxycarbonyl-(R)-(-)thiazolidine-4-carboxylic acid;3-[(2-methylpropan-2-yl)oxy-oxomethyl]-4-thiazolidinecarboxylic acid;(-)-Boc-L-thioproline, puriss. p.a., for peptide synthesis, >=99.0% (HPLC)

Chemical Property of (4R)-3-(tert-Butoxycarbonyl)-1,3-thiazolane-4-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 125-131 °C
• Refractive Index: 1.525
• Boiling Point: 385.285 °C at 760 mmHg
• PKA: 3.53±0.20(Predicted)
• Flash Point: 186.814 °C
• PSA: 92.14000
• Density: 1.306 g/cm³
• LogP: 1.31890
• Storage Temp.: −20°C
• Water Solubility.: Insoluble in water.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 233.07217913
• Heavy Atom Count: 15
• Complexity: 274

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-L-thiaproline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CSCC1C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N1CSC[C@H]1C(=O)O
• Uses: N-Boc-(R)-(-)-thiazolidine-4-carboxylic acid is used as pharmaceutical intermediates.

Technology Process of (4R)-3-(tert-Butoxycarbonyl)-1,3-thiazolane-4-carboxylic acid

There total 7 articles about (4R)-3-(tert-Butoxycarbonyl)-1,3-thiazolane-4-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + L-thioproline (34592-47-7,2756-91-4,6070-92-4,60731-25-1) → N-(tert-butoxycarbonyl)-(R)-thiazolidine-4-carboxylic acid (51077-16-8)

Guidance literature:

With triethylamine; In water; acetonitrile; at 20 ℃; for 18h;

Reference yield: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + L-thioproline (34592-47-7,2756-91-4,6070-92-4,60731-25-1) → N-tert-butoxycarbonyl-(R)-(-)thiazolidine-4-carboxylic acid (51077-16-8,63091-82-7,76587-66-1)

Guidance literature:

With triethylamine; In water; acetonitrile; at 0 - 20 ℃; for 18h;

Reference yield: 94.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + L-Cysteine (52-90-4) + di-tert-butyl dicarbonate (24424-99-5) → N-(tert-butoxycarbonyl)-(R)-thiazolidine-4-carboxylic acid (51077-16-8)

Guidance literature:

formaldehyd; L-Cysteine; With sodium hydroxide;

di-tert-butyl dicarbonate; With sodium hydroxide; In 1,4-dioxane; water;

DOI:10.1016/j.tetasy.2010.07.028

upstream raw materials:

di-tert-butyl dicarbonate

L-thioproline

L-thiazolidine-4-carboxylic acid

(RS)-4-thiazolidinecarboxylic acid

Downstream raw materials:

N-Boc-L-[2-(tert-butoxycarbonyl)phenyl]-1,3-thiazolidine-4-carboxylate

6-(4-(3-tert.-Butoxycarbonyl-L-thiazolidin-4-yl-carbonyl-amino)phenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone

C₂₇H₃₆N₂O₄S

L-thioproline

Refernces

• 1、 Chen, Tao,Reich, Nicholas William,Bell, Noah,Finn, Patricia D.,Rodriguez, David,Kohler, Jill,Kozuka, Kenji,He, Limin,Spencer, Andrew G.,Charmot, Dominique,Navre, Marc,Carreras, Christopher W.,Koo-Mccoy, Samantha,Tabora, Jocelyn,Caldwell, Jeremy S.,Jacobs, Jeffrey W.,Lewis, Jason Gustaf. "Design of Gut-Restricted Thiazolidine Agonists of G Protein-Coupled Bile Acid Receptor 1 (GPBAR1, TGR5)". supporting information. p. 7589 - 7613. Retrieved 2018/09/12.
• 2、 -. "BENZIDINE DERIVATIVE, METHOD FOR PREPARING SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING BENZIDINE DERIVATIVE FOR TREATING LIVER DISEASE CAUSED BY HEPATITIS C VIRUS". Paragraph 0177; 0178; 0179; 0180. . Retrieved 2016/02/24.