(S)-Methyl 3-amino-3-(4-chlorophenyl)propanoate

Base Information

• Chemical Name: (S)-Methyl 3-amino-3-(4-chlorophenyl)propanoate
• CAS No.: 283159-95-5
• Molecular Formula: C10H12ClNO2
• Molecular Weight: 213.66
• DSSTox Substance ID: DTXSID50368506
• Wikidata: Q72486815
• ChEMBL ID: CHEMBL4583323
• Mol file: 283159-95-5.mol

Synonyms:283159-95-5;(S)-METHYL 3-AMINO-3-(4-CHLOROPHENYL)PROPANOATE;methyl (3S)-3-amino-3-(4-chlorophenyl)propanoate;(S)-3-Amino-3-(4-Chloro-Phenyl)-Propionic Acid Methyl Ester;(S)-Methyl3-amino-3-(4-chlorophenyl)propanoate;methyl (S)-3-amino-3-(4-chlorophenyl)propanoate;SCHEMBL3658423;CHEMBL4583323;DTXSID50368506;OWKAREWNOLQNOG-VIFPVBQESA-N;AKOS016844252;BCP9000033;AS-77800;CS-0450440;EN300-147750;N16706;A876741

Chemical Property of (S)-Methyl 3-amino-3-(4-chlorophenyl)propanoate

Chemical Property:

• Boiling Point: 316.9 °C at 760 mmHg
• Flash Point: 145.4 °C
• PSA: 52.32000
• Density: 1.22 g/cm³
• LogP: 2.60320
• Storage Temp.: 2-8°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 213.0556563
• Heavy Atom Count: 14
• Complexity: 191

Purity/Quality:

99.3% ^*data from raw suppliers

Benzenepropanoicacid,?-amino-4-chloro-,methylester,(?S)- 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC(C1=CC=C(C=C1)Cl)N
• Isomeric SMILES: COC(=O)C[C@@H](C1=CC=C(C=C1)Cl)N

Technology Process of (S)-Methyl 3-amino-3-(4-chlorophenyl)propanoate

There total 5 articles about (S)-Methyl 3-amino-3-(4-chlorophenyl)propanoate 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: 79.42%

(S)-β-amino-β-(4-chlorophenyl)propionic acid (131690-60-3,131690-61-4) → methyl (S)-3-amino-3-(4-chlorophenyl)propanoate (283159-95-5)

Guidance literature:

With thionyl chloride; In methanol; at 65 ℃; for 4h;

DOI:10.1039/d1cc03392a

Reference yield: 70.0%

methyl (S)-3-(4-chlorophenyl)-3-((1,1-dimethylethyl)sulfonamido)propanoate → methyl (S)-3-amino-3-(4-chlorophenyl)propanoate (283159-95-5)

Guidance literature:

With aluminum (III) chloride; methoxybenzene; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jacs.5b04175

Reference yield:

4-chlorobenzaldehyde (104-88-1) → methyl (S)-3-amino-3-(4-chlorophenyl)propanoate (283159-95-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Amberlyst 15 / toluene / 23 h / Molecular sieve; Reflux

2.1: dimethylsulfide borane complex; (R)-3,3'-diiodo-2,2'-dihydroxy-1,1'-binaphthyl / dichloromethane; toluene / 0.5 h / 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: diazomethyl-trimethyl-silane / toluene; diethyl ether / 0.5 h / 20 °C

4.1: aluminum (III) chloride; methoxybenzene / dichloromethane / 1 h / 20 °C / Inert atmosphere

With aluminum (III) chloride; dimethylsulfide borane complex; methoxybenzene; (R)-3,3'-diiodo-2,2'-dihydroxy-1,1'-binaphthyl; diazomethyl-trimethyl-silane; In diethyl ether; dichloromethane; toluene;

DOI:10.1021/jacs.5b04175

upstream raw materials:

methanol

(S)-β-amino-β-(4-chlorophenyl)propionic acid

4-chlorobenzaldehyde

Refernces

• 1、 Morita, Yuya,Yamamoto, Tomohiro,Nagai, Hideoki,Shimizu, Yohei,Kanai, Motomu. "Chemoselective Boron-Catalyzed Nucleophilic Activation of Carboxylic Acids for Mannich-Type Reactions". . p. 7075 - 7078. Retrieved 2015/06/25.