845958-73-8

Basic information

• Product Name: METHYL (3S)-3-AMINO-3-(4-BROMOPHENYL)PROPANOATE
• Synonyms: METHYL (3S)-3-AMINO-3-(4-BROMOPHENYL)PROPANOATE;(S)-METHYL-3-AMINO-3-(4-BROMOPHENYL)PROPANOATE
• CAS NO: 845958-73-8
• Molecular Formula: C10H12BrNO2
• Molecular Weight: 258.11
• Mol File: 845958-73-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL (3S)-3-AMINO-3-(4-BROMOPHENYL)PROPANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (3S)-3-AMINO-3-(4-BROMOPHENYL)PROPANOATE(845958-73-8)
• EPA Substance Registry System: METHYL (3S)-3-AMINO-3-(4-BROMOPHENYL)PROPANOATE(845958-73-8)

Safety Data

• Hazardous Substances Data: 845958-73-8(Hazardous Substances Data)

Usage

Description

METHYL (3S)-3-AMINO-3-(4-BROMOPHENYL)PROPANOATE is a chemical compound that belongs to the class of organic compounds known as alpha amino acids and derivatives. It is a derivative of the amino acid phenylalanine, where the hydrogen at the alpha carbon is replaced by a methyl group, and the amino group is protected by a methyl ester. METHYL (3S)-3-AMINO-3-(4-BROMOPHENYL)PROPANOATE has potential therapeutic applications due to its interaction with biological receptors and enzymes in the human body. It also has potential use in the synthesis of pharmaceuticals and as a building block in organic chemistry.

Uses

Used in Pharmaceutical Industry:
METHYL (3S)-3-AMINO-3-(4-BROMOPHENYL)PROPANOATE is used as a building block for the synthesis of pharmaceuticals, contributing to the development of new drugs with potential therapeutic applications.
Used in Organic Chemistry:
METHYL (3S)-3-AMINO-3-(4-BROMOPHENYL)PROPANOATE is used as a reagent in organic chemistry, enabling the synthesis of various organic compounds and facilitating research in chemical reactions and mechanisms.
Used in Therapeutic Applications:
METHYL (3S)-3-AMINO-3-(4-BROMOPHENYL)PROPANOATE is used as a potential therapeutic agent, interacting with biological receptors and enzymes in the human body to address specific medical conditions and improve health outcomes.

Upstream product

• 67-56-1 methanol 
• 275826-36-3 (S)-3-amino-3-(4-bromophenyl)propionic acid 
• 453557-71-6 3-amino-3-(4-bromophenyl)propionic acid methyl ester 
• 39773-47-2 3-amino-3-(4'-bromophenyl)propanoic acid 

Relevant articles and documents

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.

Traceless solid-phase synthesis of chiral 3-aryl beta-amino acid containing peptides using a side-chain-tethered beta-amino acid building block.

[reaction: see text] A general method for the attachment of a chiral aromatic side-chain-containing beta-amino acid to a polymer support using a traceless silyl linkage strategy has been developed. Using this building block, solid-phase synthesis was carried out to obtain tripeptide analogues with the aromatic ring either unsubstituted or halogenated (Br, I) at the position of the silyl group. The building blocks could generate libraries of peptidomimetics or cyclic peptides containing beta-amino acids with nonpolar side chains.