283159-95-5

Basic information

• Product Name: (S)-3-AMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID METHYL ESTER
• Synonyms: (S)-METHYL 3-AMINO-3-(4-CHLOROPHENYL)PROPANOATE;(S)-3-AMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID METHYL ESTER;Methyl (3S)-3-aMino-3-(4-chlorophenyl)propanoate;methyl (S)-3-amino-3-(4-chlorophenyl)propanoate;-Methyl 3-amino-3-(4-chlorophenyl)
• CAS NO: 283159-95-5
• Molecular Formula: C₁₀H₁₂ClNO₂
• Molecular Weight: 213.66
• Mol File: 283159-95-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 316.9 °C at 760 mmHg
• Flash Point: 145.4 °C
• Appearance: /
• Density: 1.22 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (S)-3-AMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-AMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID METHYL ESTER(283159-95-5)
• EPA Substance Registry System: (S)-3-AMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID METHYL ESTER(283159-95-5)

Safety Data

• Hazardous Substances Data: 283159-95-5(Hazardous Substances Data)

Usage

General Description

(S)-3-amino-3-(4-chloro-phenyl)-propionic acid methyl ester is a chemical compound that belongs to the class of propionic acid derivatives. It is a methyl ester of (S)-3-amino-3-(4-chloro-phenyl)-propionic acid, which is an important intermediate in the synthesis of various pharmaceuticals and agrochemicals. (S)-3-AMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID METHYL ESTER has a chiral center and exists as a pair of enantiomers, with the (S)-enantiomer being the biologically active form. (S)-3-amino-3-(4-chloro-phenyl)-propionic acid methyl ester is widely used in the production of drugs that act as inhibitors of enzymes, and as a building block in organic synthesis. Its pharmacological properties and biological activities make it an important molecule in medicinal chemistry.

InChI:InChI=1S/C10H12ClNO2/c1-14-10(13)6-9(12)7-2-4-8(11)5-3-7/h2-5,9H,6,12H2,1H3

Upstream product

• 131690-60-3 (S)-β-amino-β-(4-chlorophenyl)propionic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 67-56-1 methanol 

Relevant articles and documents

Deep learning-driven scaffold hopping in the discovery of Akt kinase inhibitors

Scaffold hopping has been widely used in drug discovery and is a topic of high interest. Here a deep conditional transformer neural network, SyntaLinker, was applied for the scaffold hopping of a phase III clinical Akt inhibitor, AZD5363. A number of nove

Stereoselective chemoenzymatic preparation of β-amino esters: Molecular modelling considerations in lipase-mediated processes and application to the synthesis of (S)-dapoxetine

A wide range of optically active 3-amino-3-arylpropanoic acid derivatives have been prepared by means of a stereoselective chemoenzymatic route. The key step is the kinetic resolution of the corresponding β-amino esters. Although the enzymatic acylations of the amino group with ethyl methoxyacetate showed synthetically useful enantioselectivities, the hydrolyses of the ester group catalyzed by lipase from Pseudomonas cepacia have been identified as the optimal processes concerning both activity and enantioselectivity. The enantiopreference of this lipase in these reactions has been explained, at the molecular level, by using a fragment-based approach in which the most favoured binding site for a phenyl ring and the most stable conformation of the 3-aminopropanoate core nicely match the (S)-configuration of the major products. The conversion and enantioselectivity values of the enzymatic reactions have been compared in order to understand the influence of the different substitution patterns present in the phenyl ring. This chemoenzymatic route has been successfully applied to the preparation of a valuable intermediate in the synthesis of (S)-dapoxetine, which has been chemically synthesised in excellent optical purity.