862273-27-6

Basic information

• Product Name: 4-methylbenzenesulfonate
• Synonyms: 4-methylbenzenesulfonate;Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, methyl ester, (1R,2S)-, 4-methylbenzenesulfonate (1:1);(1R,2S)-Methyl 1-amino-2-vinylcyclopropanecarboxylate 4-methylbenzenesulfonate;methyl (1R,2S)-1-amino-2-vinylcyclopropanecarboxylate 4-methylbenzenesulfonate;(1R,2S)-1-(Methoxycarbonyl)-2-vinylcyclopropanaMiniuM 4-Methylbenzenesulfonate;Cyclopropanecarboxylic acid, 1-aMino-2-ethenyl-, Methyl ester, (1R,2S)-, 4-Methylbenzenesulfonate;(1R,2S)-Methyl 1-aMino-2-vinylcyclopropanecarboxylate PTSA;-Methyl 1-amino-2-vinylcyclopropanecarboxylate 4-methylbenzenesulfonate
• CAS NO: 862273-27-6
• Molecular Formula: C7H11NO2·C7H8O3S
• Molecular Weight: 171.19
• Mol File: 862273-27-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methylbenzenesulfonate(862273-27-6)
• EPA Substance Registry System: 4-methylbenzenesulfonate(862273-27-6)

Safety Data

• Hazardous Substances Data: 862273-27-6(Hazardous Substances Data)

Usage

Uses

(1R,2S)-Methyl 1-amino-2-vinylcyclopropanecarboxylate 4-methylbenzenesulfonate is used in the asymmetric preparation of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid.

InChI:InChI=1/C7H11NO2.C7H8O3S/c1-3-5-4-7(5,8)6(9)10-2;1-6-2-4-7(5-3-6)11(8,9)10/h3,5H,1,4,8H2,2H3;2-5H,1H3,(H,8,9,10)/t5-,7-;/m1./s1

Upstream product

• 159622-09-0 (1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid methyl ester 
• 1201943-62-5 (1R,2R)-methyl 1-t-butoxycarbonylamino-2-vinylcyclopropane carboxylate 
• 104-15-4 toluene-4-sulfonic acid 
• 213316-49-5 (1RS,2SR)-ethyl 2-vinyl-1-(tert-butoxycarbonylamino)cyclopropanecarboxylate 
• 213316-32-6 rac-(1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester 
• 1201943-62-5 1-tert-butoxycarbonylamino-2-vinylcyclopropanecarboxylic acid methyl ester 

Downstream Products

• 681260-04-8 (1R,2S)-1-amino-2-vinyl-cyclopropyl carboxylic acid methyl ester 
• 159700-58-0 (1R,2S)-2-vinyl-1-aminocyclopropanecarboxylic acid 
• 1609575-31-6 methyl 7-phenyl-6,7-dihydro[1H]azepine-2-carboxylate 

Relevant articles and documents

MACROCYCLIC HEPATITIS C PROTEASE INHIBITORS

The present invention provides novel macrocyclic compounds that mimic peptide substrates of the hepatitis C viral protease and inhibit the viral protease, more particularly as inhibitors of the NS3 serine protease from hepatitis C virus. Methods for synthesis of the compounds are also provided. The compounds find utility as antiviral agents directed at hepatitis C. The invention further provides methods of employing such inhibitors, alone or in combination with other therapeutic agents, to treat hepatitis C infection in a subject in need of such treatment.

Synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid vinyl-ACCA derivatives: Key intermediates for the preparation of inhibitors of the hepatitis C virus NS3 protease

(1R,2S)-1-Amino-2-vinylcyclopropanecarboxylic acid (vinyl-ACCA) is a key building block in the synthesis of potent inhibitors of the hepatitis C virus NS3 protease such as BILN 2061, which was recently shown to dramatically reduce viral load after administration to patients infected with HCV genotype 1. We have developed a scalable process that delivers derivatives of this unusual amino acid in >99% ee. The strategy was based on the dialkylation of a glycine Schiff base using trans-1,4-dibromo-2-butene as an electrophile to produce racemic vinyl-ACCA, which was subsequently resolved using a readily available, inexpensive esterase enzyme (Alcalase 2.4L). Factors that affect diastereoselection in the initial dialkylation steps were examined and the conditions optimized to deliver the desired diastereomer selectively. Product inhibition, which was encountered during the enzymatic resolution step, initially resulted in prolonged cycle times. Enrichment of racemic vinyl-ACCA through a chemical resolution via diastereomeric salt formation or the use of forcing conditions in the enzymatic reaction both led to improvements in throughput and the development of a viable process. The chemistry described herein was scaled up to produce multikilogram quantities of this building block.