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

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

Used in Organic Synthesis:
4-methylbenzenesulfonate is used as a protecting group in organic synthesis for the selective protection of functional groups, such as alcohols and amines. Its stability and ease of removal make it a valuable tool in the synthesis of complex organic molecules.
Used in Asymmetric Synthesis:
4-methylbenzenesulfonate is used as a chiral auxiliary in asymmetric synthesis to control the stereochemistry of reactions. Its chiral center can influence the outcome of reactions, leading to the formation of enantiomerically pure products.
Used in the Asymmetric Preparation of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic Acid:
4-methylbenzenesulfonate is used as a reagent in the asymmetric preparation of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid. Its use in this process allows for the selective formation of the desired enantiomer, which is important for the development of chiral drugs and other enantioselective applications.
Used in Pharmaceutical Industry:
4-methylbenzenesulfonate is used as an intermediate in the synthesis of various pharmaceutical compounds. Its versatility and reactivity make it a valuable building block for the development of new drugs and therapeutic agents.
Used in Chemical Research:
4-methylbenzenesulfonate is used as a research tool in the study of reaction mechanisms and the development of new synthetic methods. Its unique properties allow chemists to probe the fundamental aspects of organic reactions and develop new strategies for the synthesis of complex molecules.

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

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

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.

Epimerization reaction of a substituted vinylcyclopropane catalyzed by ruthenium carbenes: Mechanistic analysis

A novel ruthenium carbene-catalyzed epimerization of vinylcyclopropanes is reported. The reaction rate strongly depends on the presence of ruthenium ligands in solution. When the first-generation Grubbs catalyst is employed, a 5.3:1 equilibrium ratio of epimers is established quickly, but when a first-generation Hoveyda catalyst is employed, epimerization is observed only if an additional phosphine or nitrogen ligand is added. NMR and kinetic studies suggest that the isomerization reaction occurs through the intermediacy of a ruthenacyclopentene. The observation suggests that cyclopropylmethylidene ruthenium carbenes of synthetic utility may be accessible via ruthenacyclopentenes obtained via other routes.

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.