2-Benzoylamino-4-methylsulfanyl-butyric acid methyl ester

Base Information

• Chemical Name: 2-Benzoylamino-4-methylsulfanyl-butyric acid methyl ester
• CAS No.: 50732-06-4
• Molecular Formula: C13H17 N O3 S
• Molecular Weight: 267.349
• Hs Code.: 2930909090
• European Community (EC) Number: 256-744-3
• NSC Number: 164033
• Nikkaji Number: J1.110.750H
• Mol file: 50732-06-4.mol

Synonyms:2-Benzoylamino-4-methylsulfanyl-butyric acid methyl ester;39608-60-1;Methyl N-benzoyl-L-methionate;EINECS 256-744-3;SCHEMBL18095164;benzoyl-dl-methionine methyl ester;NSC164033;AKOS000676048;AKOS024307930;AB02074;NSC 164033;NSC-164033;METHYL 2-BENZAMIDO-4-(METHYLTHIO)BUTANOATE;METHYL2-BENZAMIDO-4-(METHYLTHIO)BUTANOATE;SR-01000318266;SR-01000318266-1

Chemical Property of 2-Benzoylamino-4-methylsulfanyl-butyric acid methyl ester

Chemical Property:

• Vapor Pressure: 4.22E-09mmHg at 25°C
• Boiling Point: 472.6°C at 760 mmHg
• Flash Point: 239.6°C
• PSA: 80.70000
• Density: 1.161g/cm³
• LogP: 2.10200
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 267.09291458
• Heavy Atom Count: 18
• Complexity: 277

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CCSC)NC(=O)C1=CC=CC=C1

Technology Process of 2-Benzoylamino-4-methylsulfanyl-butyric acid methyl ester

There total 2 articles about 2-Benzoylamino-4-methylsulfanyl-butyric acid 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:

methanol (67-56-1) + 4-(2-methylsulfanyl-ethyl)-2-phenyl-4H-oxazol-5-one (51127-20-9,71963-73-0,150072-83-6) → methyl benzoyl-L-methioninate (50732-06-4) + (R)-2-Benzoylamino-4-methylsulfanyl-butyric acid methyl ester

Guidance literature:

With planar-chiral DMAP-ferrocene derivative; benzoic acid; In toluene; Product distribution; Ambient temperature; methanolysis of azlactones dynamic kinetic resolution of azlactones; enantiomeric excess; solvent effect on enantioselectivity; reaction with other alcohols; effect of steric factors on enantioselectivity;

DOI:10.1021/jo9803380

Reference yield:

(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride (2491-18-1) → methyl benzoyl-L-methioninate (50732-06-4)

Guidance literature:

With bicarbonate; benzoylation;

DOI:10.1016/S0040-4020(01)87715-2

Reference yield: 87.0%

methyl benzoyl-L-methioninate (50732-06-4) → (S)-N-[1-hydroxy-4-(methylthio)butan-2-yl]benzamide (1303536-70-0)

Guidance literature:

methyl benzoyl-L-methioninate; With sodium tetrahydroborate; In tetrahydrofuran; at 65 ℃; for 0.25h;

With methanol; In tetrahydrofuran; at 65 ℃; stereospecific reaction;

DOI:10.1080/00397911.2010.481747

upstream raw materials:

methanol

4-(2-methylsulfanyl-ethyl)-2-phenyl-4H-oxazol-5-one

(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride

Downstream raw materials:

N-benzoyl L-methionine sulphoxide

Bz-Met(sulfoxide)-OMe

BzNHCH(CH₂CH₂SO₂H)COOMe

Bz-Met(sulfone)-OMe

Refernces

• 1、 Liang, Jack,Ruble, Craig,Fu, Gregory C.. "Dynamic Kinetic Resolutions Catalyzed by a Planar-Chiral Derivative of DMAP: Enantioselective Synthesis of Protected α-Amino Acids from Racemic Azlactones". . p. 3154 - 3155. Retrieved 2007/10/03.
• 2、 Ranganathan, S.,Ranganathan, D.,Singh, S.K.,Bhattacharyya, D.,Shanthy, S.,Singh, G.P.. "L-METHIONINE OXIDATION: NOVEL AND UNANTICIPATED TRANSFORMATIONS WITH 4-tBUTYL IODOXYBENZENE". . p. 5363 - 5366. Retrieved 2007/10/02.