N-Benzoyl-L-threonine methyl ester

Base Information

• Chemical Name: N-Benzoyl-L-threonine methyl ester
• CAS No.: 79893-89-3
• Molecular Formula: C12H15 N O4
• Molecular Weight: 237.255
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID30352948
• Nikkaji Number: J807.495J
• Wikidata: Q82130385
• ChEMBL ID: CHEMBL1878775
• Mol file: 79893-89-3.mol

Synonyms:N-Benzoyl-L-threonine methyl ester;79893-89-3;BZ-THR-OME;(2S,3R)-Methyl 2-benzamido-3-hydroxybutanoate;methyl (2S,3R)-2-benzamido-3-hydroxybutanoate;MFCD00010394;SMR000639435;Benzoyl-D-threonine methyl ester;N-Benzoylthreonine methyl ester;methyl N-benzoylthreoninate;MLS001075372;MLS001075435;SCHEMBL160178;CHEMBL1878775;DTXSID30352948;KHOWDUMYRBCHAC-SCZZXKLOSA-N;HMS2194G18;AKOS005258790;HY-W142106;n,n-dimethyl-2-(2-aminoethoxy)ethanol;MS-20228;N-Benzoyl-L-threonine methyl ester, 99%;CS-0201890;E77608;methyl (2S,3R)-2-benzamido-3-hydroxy-butanoate;A839782;A840014;methyl (2S,3R)-2-benzamido-3-oxidanyl-butanoate;methyl (2S,3R)-3-hydroxy-2-(phenylformamido)butanoate;(2S,3R)-2-benzamido-3-hydroxybutanoic acid methyl ester;N-alpha-BenZoyl-L-threonine methyl ester (BZ-L-Thr-OMe)

Chemical Property of N-Benzoyl-L-threonine methyl ester

Chemical Property:

• Vapor Pressure: 1.17E-09mmHg at 25°C
• Melting Point: 97-99 °C(lit.)
• Refractive Index: 1.536
• Boiling Point: 470.6oC at 760 mmHg
• PKA: 12.96±0.46(Predicted)
• Flash Point: 238.4oC
• PSA: 75.63000
• Density: 1.2g/cm3
• LogP: 0.72970
• Storage Temp.: Store at RT.
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 237.10010796
• Heavy Atom Count: 17
• Complexity: 274

Purity/Quality:

99%, ^*data from raw suppliers

N-Benzoyl-L-threonine methyl ester 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C(=O)OC)NC(=O)C1=CC=CC=C1)O
• Isomeric SMILES: C[C@H]([C@@H](C(=O)OC)NC(=O)C1=CC=CC=C1)O

Technology Process of N-Benzoyl-L-threonine methyl ester

There total 16 articles about N-Benzoyl-L-threonine methyl ester 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: 96.0%

L-threonine methyl ester hydrochloride (39994-75-7) + benzoyl chloride (98-88-4) → N-benzoyl-L-threonine methyl ester (79893-89-3)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo5016695

Reference yield: 95.0%

L-threonine methyl ester (3373-59-9) + benzoyl chloride (98-88-4) → N-benzoyl-L-threonine methyl ester (79893-89-3)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1002/chem.200204649

Reference yield: 92.0%

methyl L-threoninate hydrochloride + benzoyl chloride (98-88-4) → N-benzoyl-L-threonine methyl ester (79893-89-3)

Guidance literature:

methyl L-threoninate hydrochloride; With triethylamine; In methanol; at 20 ℃; for 0.25h;

benzoyl chloride; In methanol; at 0 ℃; for 2.16667h;

upstream raw materials:

diazomethane

(2S,3R)-threo-N-benzoyl-threonine

L-threonine methyl ester hydrochloride

benzoyl chloride

Downstream raw materials:

(2R,3S)-N-benzoylthreonine methyl ester

(2S,3R)-threo-N-benzoyl-threonine

(2S,3S)-erythro-N-benzoyl-threonine

methyl N-benzoyl (2R,3R)-allo-threoninate

Refernces

• 1、 Ozaki, Yui,Yamada, Tomoaki,Mizuno, Taisei,Osaka, Kazuyuki,Yamawaki, Mugen,Maeda, Hajime,Morita, Toshio,Yoshimi, Yasuharu. "Retention of chirality of 5-membered alicyclic α-amino acids bearing N-(2-phenyl)benzoyl group in photoinduced decarboxylative intermolecular radical addition to acrylonitrile". . . Retrieved 2019/08/08.
• 2、 Lin, Zhenjian,Smith, Misty D.,Concepcion, Gisela P.,Haygood, Margo G.,Olivera, Baldomero M.,Light, Alan,Schmidt, Eric W.. "Modulating the Serotonin Receptor Spectrum of Pulicatin Natural Products". . p. 2360 - 2370. Retrieved 2017/09/01.