93634-74-3

Basic information

• Product Name: (S)-(+)-p-chloro-N-acetyl-L-phenylalanine methyl ester
• Synonyms: (S)-(+)-p-chloro-N-acetyl-L-phenylalanine methyl ester;(S)-Methyl 2-acetylamino-3-(4-chlorophenyl)propanoate;N-Acetyl L-4-chlorophenylalanine methyl ester;N-Acetyl-4-chloro-L-phenylalanine methyl ester
• CAS NO: 93634-74-3
• Molecular Formula: C12H14ClNO3
• Molecular Weight: 0
• Mol File: 93634-74-3.mol
• Article Data: 85

Chemical Properties

• Appearance: /
• Density: 1.217
• CAS DataBase Reference: (S)-(+)-p-chloro-N-acetyl-L-phenylalanine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-p-chloro-N-acetyl-L-phenylalanine methyl ester(93634-74-3)
• EPA Substance Registry System: (S)-(+)-p-chloro-N-acetyl-L-phenylalanine methyl ester(93634-74-3)

Safety Data

• Hazardous Substances Data: 93634-74-3(Hazardous Substances Data)

Usage

Description

(S)-(+)-p-chloro-N-acetyl-L-phenylalanine methyl ester is a chiral chemical compound that is widely utilized in pharmaceutical research and development. As an enantiomer of N-acetyl-L-phenylalanine methyl ester, it possesses a distinct chirality that differentiates it from its counterpart. (S)-(+)-p-chloro-N-acetyl-L-phenylalanine methyl ester is recognized for its potential pharmaceutical applications, particularly in the creation of innovative drugs and medications. Its unique structure and properties render it a valuable asset in the study of drug interactions and the mechanisms of action.

Uses

Used in Pharmaceutical Research and Development:
(S)-(+)-p-chloro-N-acetyl-L-phenylalanine methyl ester is used as a key compound in the synthesis of various molecules with therapeutic properties. Its unique structure allows researchers to explore its potential in developing novel drugs and medications, contributing to the advancement of the pharmaceutical industry.
Used in Chemical and Biological Research:
In the fields of chemical and biological research, (S)-(+)-p-chloro-N-acetyl-L-phenylalanine methyl ester is employed to investigate its effects on different physiological processes and pathways. This helps in understanding the compound's role in biological systems and its potential applications in the development of targeted therapies and treatments for various diseases and conditions.

Upstream product

• 102245-02-3 methyl (Z)-2-acetylamino-3-(4-chlorophenyl)-2-propenoate 
• 312300-60-0 methyl (E)-2-acetylamino-3-(4-chlorophenyl)-2-propenoate 
• 23633-07-0 2-amino-3-(4-chlorophenyl)propionic acid hydrochloride 
• 14173-40-1 2-amino-3-(4-chlorophenyl)propionic acid methyl ester hydrochloride 
• 129496-71-5 methyl 2-acetylamino-3-(4-chlorophenyl)propanoate 
• 109-21-7 butyl butyrate 
• 20877-13-8 ethyl 2-acetylamino-3-(4-chlorophenyl)-2-cyanopropanoate 
• 622-95-7 4-chlorobenzyl bromide 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 104-88-1 4-chlorobenzaldehyde 
• 93634-55-0 (Z)-4-(4-chlorobenzylidene)-2-methyloxazol-5(4H)-one 
• 35356-70-8 Methyl 2-acetamidoacrylate 
• 1679-18-1 4-Chlorophenylboronic acid 
• 93634-55-0 2-methyl-4-(4-chlorobenzylidene)-4H-oxazol-5-one 

Relevant articles and documents

Mechanistically Guided One Pot Synthesis of Phosphine-Phosphite and Its Implication in Asymmetric Hydrogenation

Although hybrid bidentate ligands are known to yield highly enantioselective products in asymmetric hydrogenation (AH), synthesis of these ligands is an arduous process. Herein, a one pot, atom-economic synthesis of a hybrid phosphine-phosphite (L1) is reported. After understanding the reactivity difference between an O-nucleophile versus C-nucleophile, one pot synthesis of Senphos (L1) was achieved (72 %). When L1 was treated with [Rh], 31P NMR revealed bidentate coordination to Rh. Senphos, in the presence of rhodium, catalyzes the AH of Methyl-2-acetamido-3-phenylacrylate and discloses an unprecedented turn over frequency of 2289, along with excellent enantio-selectivity (92 %). The generality is demonstrated by hydrogenating an array of alkenes. The AH operates under mild conditions of 1–2 bar H2 pressure, at room temperature. The practical relevance of L1 is demonstrated by scaling-up the reaction to 1 g and by synthesizing DOPA, a drug widely employed for the treatment of Parkinson's disease. Computational insights indicate that the R isomer is preferred by 3.8 kcal/mol over the S isomer.

Diaza-Crown Ether-Bridged Chiral Diphosphoramidite Ligands: Synthesis and Applications in Asymmetric Catalysis

A small library of diaza-crown ether-bridged chiral diphosphoramidite ligands was prepared. In the rhodium-catalyzed asymmetric hydrogenation and hydroformylation reactions, these ligands exhibited distinct properties in catalytic activity and/or enantioselectivity. Hydrogenated products with opposite absolute configurations could be obtained in high yields with excellent ee values by utilizing (S,S)-L1 and (S,S)-L3, respectively. Meanwhile, the addition of alkali metal cations caused variations in catalytic outcomes, showing the supramolecular tunability of these Rh/diphosphoramidite catalytic systems.

Asymmetric Synthesis of Chiral Spiroketal Bisphosphine Ligands and Their Application in Enantioselective Olefin Hydrogenation

A series of chiral spiroketal bisphosphine ligands containing 1,1′-spirobi(3H,3′H)isobenzofuran backbones was accessed through asymmetric synthesis and subsequently tested in enantioselective Rh-catalyzed hydrogenation of α-dehydroamino acid esters. The l