(S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxy-2-methylpropanoic acid

Base Information

• Chemical Name: (S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxy-2-methylpropanoic acid
• CAS No.: 84311-19-3
• Molecular Formula: C9H17 N O5
• Molecular Weight: 219.238
• Hs Code.: 2924 19 00
• DSSTox Substance ID: DTXSID501004616
• Nikkaji Number: J2.213.648H
• Wikidata: Q82999704
• Mol file: 84311-19-3.mol

Synonyms:84311-19-3;(S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxy-2-methylpropanoic acid;N-Boc-alpha-methyl-L-serine;(2S)-3-hydroxy-2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;BOC-D-ALPHA-METHYLSERINE;N-(Boc)-a-methylserine;BOC-ALPHA-METHYL-L-SER;Serine, N-[(1,1-dimethylethoxy)carbonyl]-2-methyl-;N-(Boc)-alpha-methylserine;N-{[(1,1-Dimethylethyl)oxy]carbonyl}-2-methylserine;SCHEMBL1486204;BOC-L-ALPHA-METHYLSERINE;BOC-(S)-2-AMINO-2-METHYL-3-HYDROXYPROPANOIC ACID;FWRXDSRYWWYTPD-VIFPVBQESA-N;DTXSID501004616;AMY37545;(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxy-2-methylpropanoic acid;MFCD02682593;(S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-HYDROXY-2-METHYLPROPANOIC ACID;AKOS016843698;AB12256;AS-47659;N-Boc-alpha-methyl-L-serine, AldrichCPR;CS-0137988;Boc-|A inverted exclamation mark-methyl-L-Ser;F15068;N-Boc-alpha-methyl-L-serine (Boc-L-aMeSer-OH);A840757;N-[tert-Butoxy(hydroxy)methylidene]-2-methylserine;N-{[(1,1-Dimethylethyl)oxy]carbonyl}-2-methyl-L-serine;Serine,N-[(1,1-dimethylethoxy)carbonyl]-2-methyl-(9ci);(S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxy-2-methylpropanoicacid;(S)-2-tert-Butoxycarbonylamino-3-hydroxy-2-methyl-propionic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxy-2-methylpropanoic acid

Chemical Property of (S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxy-2-methylpropanoic acid

Chemical Property:

• Vapor Pressure: 1.36E-07mmHg at 25°C
• Melting Point: 126°C
• Boiling Point: 387.1oC at 760 mmHg
• Flash Point: 187.9oC
• PSA: 95.86000
• Density: 1.207g/cm3
• LogP: 0.73760
• Storage Temp.: Store below +30°C.
• Solubility.: Soluble in dimethylformamide.
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 219.11067264
• Heavy Atom Count: 15
• Complexity: 258

Purity/Quality:

98% ^*data from raw suppliers

Boc-Ser(Me)-OH Novabiochem . CAS 84311-19-3, molar mass 219.24 g/mol., Novabiochem ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C)(CO)C(=O)O
• Isomeric SMILES: C[C@](CO)(C(=O)O)NC(=O)OC(C)(C)C
• Uses: N-Boc-2-methyl-L-serine is used as a cocatalyst in the Diels-Alder reactions between cyclopentadiene and methyl acrylate in the presence of Lewis acids.

Technology Process of (S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxy-2-methylpropanoic acid

There total 1 articles about (S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxy-2-methylpropanoic 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: 97.0%

(S)-(+)-2-amino-2-methyl-3-hydroxypropanoic acid (3398-40-1,5424-29-3,16820-18-1,81132-44-7) + di-tert-butyl dicarbonate (24424-99-5) → (S)-2-tert-Butoxycarbonylamino-3-hydroxy-2-methyl-propionic acid (84311-19-3)

Guidance literature:

With sodium hydroxide; triethylamine; In methanol; at 20 ℃;

DOI:10.1021/jm070476u

Reference yield: 91.0%

glycine benzyl ester p-toluenesulfonic acid salt (1738-76-7) + (S)-2-tert-Butoxycarbonylamino-3-hydroxy-2-methyl-propionic acid (84311-19-3) → C18H26N2O6

Guidance literature:

(S)-2-tert-Butoxycarbonylamino-3-hydroxy-2-methyl-propionic acid; With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.166667h;

glycine benzyl ester p-toluenesulfonic acid salt; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1111/cbdd.12305

Reference yield: 86.0%

α-bromomethyl p(n-octyl)phenyl cetone (64068-76-4) + (S)-2-tert-Butoxycarbonylamino-3-hydroxy-2-methyl-propionic acid (84311-19-3) → (2S)-2-tert-butoxycarbonylamino-3-hydroxy-2-methylpropionic acid 2-(4-octyl-phenyl)-2-oxo-ethyl ester (1190087-34-3)

Guidance literature:

(S)-2-tert-Butoxycarbonylamino-3-hydroxy-2-methyl-propionic acid; With caesium carbonate; In ethanol; Sonication;

α-bromomethyl p(n-octyl)phenyl cetone; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmc.2009.04.015

upstream raw materials:

(S)-(+)-2-amino-2-methyl-3-hydroxypropanoic acid

di-tert-butyl dicarbonate

Downstream raw materials:

(S)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxypropanoic acid methyl ester

tert-butyl (S)-2-(4-hydroxyphenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate

tert-butyl (S)-2-(4-(2-biphenyl-4-ylethyloxy)phenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate

tert-butyl (S)-2-(4-(4-(4-phenylphenyl)butan-2-yloxy)phenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate

Refernces

• 1、 Yu, Weiping,McConathy, Jonathan,Williams, Larry,Camp, Vernon M.,Malveaux, Eugene J.,Zhang, Zhaobin,Olson, Jeffrey J.,Goodman, Mark M.. "Synthesis, radiolabeling, and biological evaluation of (R)- and (S)-2-amino-3-[18F]fluoro-2-methylpropanoic acid (FAMP) and (R)- and (S)-3-[18F]fluoro-2-methyl-2-n-(methylamino)propanoic acid (NMeFAMP) as potential PET radioligands for imaging brain tumors". experimental part. p. 876 - 886. Retrieved 2010/07/05.
• 2、 Yu, Weiping,McConathy, Jonathan,Olson, Jeffrey,Camp, Vernon M.,Goodman, Mark M.. "Facile stereospecific synthesis and biological evaluation of (S)- and (R)-2-amino-2-methyl-4-[123I]iodo-3-(E)-butenoic acid for brain tumor imaging with single photon emission computerized tomography". . p. 6718 - 6721. Retrieved 2008/09/17.