Butanoic acid, 3-(phenylamino)-, methyl ester, (R)-

Base Information

• Chemical Name: Butanoic acid, 3-(phenylamino)-, methyl ester, (R)-
• CAS No.: 63430-94-4
• Molecular Formula: C11H15NO2
• Molecular Weight: 193.246
• DSSTox Substance ID: DTXSID60462620
• Nikkaji Number: J2.249.345K
• Wikidata: Q82287180
• Mol file: 63430-94-4.mol

Synonyms:63430-94-4;Butanoic acid, 3-(phenylamino)-, methyl ester, (R)-;SCHEMBL22950649;DTXSID60462620

Chemical Property of Butanoic acid, 3-(phenylamino)-, methyl ester, (R)-

Chemical Property:

• 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:

SDS file from LookChem

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 Butanoic acid, 3-(phenylamino)-, methyl ester, (R)-

There total 3 articles about Butanoic acid, 3-(phenylamino)-, methyl ester, (R)- 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: 81.0%

Methyl (R)-3-hydroxybutyrate (3976-69-0) + acetoacetic acid methyl ester (105-45-3) + aniline (62-53-3) → methyl (R)-3-(phenylamino)butanoate (63430-94-4) + (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; In pyridine; dichloromethane; at 0 ℃; for 1h;

aniline; at -40 ℃; for 16h;

Reference yield:

methyl 3-phenylaminobut-2-enoate (4916-22-7,40801-08-9) → methyl (R)-3-(phenylamino)butanoate (63430-94-4) + (S)-phenylamino-butyric acid methyl ester (142826-92-4)

Guidance literature:

With bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; hydrogen; triphenylphosphine; (S)-(+)-(3,5-dioxa-4-phosphacyclohepta[2,1-a:3,4-a']-dinaphthalen-4-yl)piperidine; In dichloromethane; at 20 ℃; for 16h; under 18751.9 Torr; enantioselective reaction; Autoclave;

DOI:10.1016/j.tetasy.2010.11.026

upstream raw materials:

Methyl (R)-3-hydroxybutyrate

acetoacetic acid methyl ester

aniline

methyl 3-phenylaminobut-2-enoate