Benzyl 2-(2-benzyl-3-mercaptopropanamido)acetate

Base Information

• Chemical Name: Benzyl 2-(2-benzyl-3-mercaptopropanamido)acetate
• CAS No.: 81110-69-2
• Molecular Formula: C19H21NO3S
• Molecular Weight: 343.44
• UNII: 2TPS4YR8V8
• Mol file: 81110-69-2.mol

Synonyms:81110-69-2;Deacetyl Racecadotril;Benzyl 2-(2-benzyl-3-mercaptopropanamido)acetate;2TPS4YR8V8;UNII-2TPS4YR8V8;Racecadotril impurity G [EP];benzyl 2-[(2-benzyl-3-sulfanylpropanoyl)amino]acetate;Benzyl (((2RS)-2-benzyl-3-sulfanylpropanoyl)amino)acetate;Glycine, N-(2-(mercaptomethyl)-1-oxo-3-phenylpropyl)-, phenylmethyl ester;n-[2-(mercaptomethyl)-1-oxo-3-phenylpropyl]glycine phenylmethyl ester;n-(2-(mercaptomethyl)-1-oxo-3-phenylpropyl)glycine phenylmethyl ester;SCHEMBL9096963;RACECADOTRIL IMPURITY G [EP IMPURITY]

Chemical Property of Benzyl 2-(2-benzyl-3-mercaptopropanamido)acetate

Chemical Property:

• PSA: 94.20000
• LogP: 3.02560
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 343.12421471
• Heavy Atom Count: 24
• Complexity: 390

Purity/Quality:

97% ^*data from raw suppliers

DeacetylRacecadotril ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(CS)C(=O)NCC(=O)OCC2=CC=CC=C2

Technology Process of Benzyl 2-(2-benzyl-3-mercaptopropanamido)acetate

There total 4 articles about Benzyl 2-(2-benzyl-3-mercaptopropanamido)acetate 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%

{2-[2-(Benzyloxycarbonylmethyl-carbamoyl)-3-phenyl-propyldisulfanylmethyl]-3-phenyl-propionylamino}-acetic acid benzyl ester (141437-88-9) → N-(2-mercaptomethyl-3-phenyl-1-oxopropyl)-glycine benzyl ester (81110-69-2)

Guidance literature:

With hydrogenchloride; zinc; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jm00091a016

Reference yield: 88.0%

racecadotril (81110-73-8) → N-(2-mercaptomethyl-3-phenyl-1-oxopropyl)-glycine benzyl ester (81110-69-2)

Guidance literature:

With propylamine; tributylphosphine; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/jacs.1c02606

Reference yield: 76.0%

→ N-(2-mercaptomethyl-3-phenyl-1-oxopropyl)-glycine benzyl ester (81110-69-2)

Guidance literature:

upstream raw materials:

{2-[2-(Benzyloxycarbonylmethyl-carbamoyl)-3-phenyl-propyldisulfanylmethyl]-3-phenyl-propionylamino}-acetic acid benzyl ester

2-(2-Carboxy-3-phenyl-propyldisulfanylmethyl)-3-phenyl-propionic acid

racecadotril

Downstream raw materials:

3-[2-(Benzyloxycarbonylmethyl-carbamoyl)-3-phenyl-propylsulfanylcarbonyl]-propionic acid tert-butyl ester

[2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentyldisulfanylmethyl)-3-phenyl-propionylamino]-acetic acid benzyl ester

[2-((S)-2-tert-Butoxycarbonylamino-4-methylsulfanyl-butyldisulfanylmethyl)-3-phenyl-propionylamino]-acetic acid benzyl ester

[2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propyldisulfanylmethyl)-3-phenyl-propionylamino]-acetic acid benzyl ester