Methyl (3S)-3-(phenylamino)butanoate

Base Information

• Chemical Name: Methyl (3S)-3-(phenylamino)butanoate
• CAS No.: 142826-92-4
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.246
• European Community (EC) Number: 604-313-9
• DSSTox Substance ID: DTXSID401291228
• Nikkaji Number: J953.821F
• Mol file: 142826-92-4.mol

Synonyms:SCHEMBL2386328;DTXSID401291228;Methyl (3S)-3-(phenylamino)butanoate;142826-92-4

Chemical Property of Methyl (3S)-3-(phenylamino)butanoate

Chemical Property:

• Vapor Pressure: 0.00043mmHg at 25°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 193.110278721
• Heavy Atom Count: 14
• Complexity: 176

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CC(=O)OC)NC1=CC=CC=C1
• Isomeric SMILES: C[C@@H](CC(=O)OC)NC1=CC=CC=C1

Technology Process of Methyl (3S)-3-(phenylamino)butanoate

There total 8 articles about Methyl (3S)-3-(phenylamino)butanoate 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: 94.0%

Methyl (R)-3-hydroxybutyrate (3976-69-0) + aniline (62-53-3) → methyl (R)-3-(phenylamino)butanoate (63430-94-4) + (S)-phenylamino-butyric acid methyl ester (142826-92-4)

Guidance literature:

Methyl (R)-3-hydroxybutyrate; With trifluoromethanesulfonic acid anhydride; diisopropylamine; In dichloromethane; at -78 ℃; for 1h;

aniline; at -78 - -40 ℃; for 16h;

Reference yield: 90.0%

methanol (67-56-1) + (S)-(+)-N-(3-phenylaminobutyryl)benzoic acid (142925-36-8) → (S)-phenylamino-butyric acid methyl ester (142826-92-4)

Guidance literature:

With thionyl chloride; water; at 20 ℃; for 12h;

DOI:10.1016/j.bmcl.2009.10.094

Reference yield: 88.0%

Methyl (R)-3-hydroxybutyrate (3976-69-0) + acetoacetic acid methyl ester (105-45-3) + aniline (62-53-3) → (S)-phenylamino-butyric acid methyl ester (142826-92-4)

Guidance literature:

acetoacetic acid methyl ester; With hydrogen; RuCl₂ (R)-binap; In methanol; at 80 ℃; for 66h; under 22801.5 Torr;

Methyl (R)-3-hydroxybutyrate; With trifluoromethanesulfonic acid anhydride; In pyridine; dichloromethane; at 0 ℃; for 1h;

aniline; at 25 ℃; for 16h;

upstream raw materials:

methanol

(S)-(+)-N-(3-phenylaminobutyryl)benzoic acid

aniline

bromobenzene

Downstream raw materials:

(S)-(+)-N-(3-phenylaminobutyryl)benzoic acid

(S)-3-(phenylamino)butan-1-ol

C₁₈H₁₉NO₃