159622-09-0

Basic information

• Product Name: methyl ester, (1R,2S)-
• Synonyms: methyl ester, (1R,2S)-;methyl (1R,2S)-1-[(tert-butoxycarbonyl)amino]-2-vinylcyclopropanecarboxylate;Cyclopropanecarboxylic acid, 1-[[(1,1-diMethylethoxy)carbonyl]aMino]-2-ethenyl-, Methyl ester, (1R,2S)-;(1R,2S)-1-[[(1,1-DiMethylethoxy)Carbonyl]AMino]-2-Ethenyl-Cyclopropanecarboxylic Acid Methyl Ester;(1R,2S)-Methyl 1-(tert-butoxycarbonylamino)- 2-vinylcyclopropanecarboxylate
• CAS NO: 159622-09-0
• Molecular Formula: C₁₂H₁₉NO₄
• Molecular Weight: 241.285
• Mol File: 159622-09-0.mol

Chemical Properties

• Boiling Point: 312.253°C at 760 mmHg
• Flash Point: 142.646°C
• Appearance: /
• Density: 1.101g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.484
• Storage Temp.: 2-8°C
• CAS DataBase Reference: methyl ester, (1R,2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: methyl ester, (1R,2S)-(159622-09-0)
• EPA Substance Registry System: methyl ester, (1R,2S)-(159622-09-0)

Safety Data

• Hazardous Substances Data: 159622-09-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Methyl ester, (1R,2S)is utilized as a building block in organic synthesis for the production of pharmaceuticals, fragrances, and flavorings. Its chiral nature allows for the creation of enantiomerically pure compounds, which are essential in the development of effective and safe medications.
Used in Asymmetric Synthesis:
Due to its chiral properties, methyl ester, (1R,2S)is employed in asymmetric synthesis, a technique that selectively produces one enantiomer of a chiral compound over the other. This is crucial in the pharmaceutical industry, as different enantiomers can have different biological activities and side effects.
Used as a Solvent:
Methyl ester, (1R,2S)can also function as a solvent in various chemical processes. Its unique properties may offer advantages over traditional solvents, such as improved solubility or selectivity in certain reactions.
Used as an Intermediate in Chemical Reactions:
In addition to its direct applications, methyl ester, (1R,2S)serves as an intermediate in a range of chemical reactions. Its presence can facilitate the synthesis of more complex molecules or enable the production of other valuable compounds through subsequent reactions.

InChI:InChI=1/C12H19NO4/c1-6-8-7-12(8,9(14)16-5)13-10(15)17-11(2,3)4/h6,8H,1,7H2,2-5H3,(H,13,15)/t8-,12-/m1/s1

Upstream product

• 159622-08-9 (1S,2S)-1-Azidocarbonyl-2-vinyl-cyclopropanecarboxylic acid methyl ester 
• 75-65-0 tert-butyl alcohol 
• 1201943-62-5 1-tert-butoxycarbonylamino-2-vinylcyclopropanecarboxylic acid methyl ester 
• 67-56-1 methanol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 213316-32-6 rac-(1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester 
• 213316-49-5 (1RS,2SR)-ethyl 2-vinyl-1-(tert-butoxycarbonylamino)cyclopropanecarboxylate 
• 17447-60-8 dimethyl 2-vinylcyclopropane-1,1-dicarboxylate 
• 259214-58-9 (1S,2S)-1-amino-2-vinylcyclopropane carboxylic acid methyl-ester hydrochloride 
• 915317-20-3 C₁₂H₁₉NO₄ 
• 159700-58-0 (1R,2S)-2-vinyl-1-aminocyclopropanecarboxylic acid 
• 159622-10-3 (1R,2S)-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 681260-04-8 (1R,2S)-1-amino-2-vinyl-cyclopropyl carboxylic acid methyl ester 

Downstream Products

• 159622-10-3 (1R,2S)-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid 
• 862273-27-6 (1R,2S)-1-amino-2-vinylcyclopropane carboxylic acid methyl ester tosylate salt 
• 1201943-62-5 (1R,2R)-methyl 1-t-butoxycarbonylamino-2-vinylcyclopropane carboxylate 
• 862273-27-6 (1R,2R)-methyl 1-amino-2-vinylcyclopropane carboxylate tosylate salt 
• 853269-57-5 tert-butyl [(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]carbamate 

Relevant articles and documents

A TEIXOBACTIN ANALOGUE AND USE THEREOF

Provided herein belongs to the field of pharmaceuticals, and specifically relates to a Teixobactin analogue and use thereof. It further relates to a pharmaceutical composition comprising the compound and use of the compound and the pharmaceutical composit

Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral Ni(II) complex of glycine Schiff base

Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid (vinyl-ACCA) is in extremely high demand due to the pharmaceutical importance of this tailor-made, sterically constrained α-amino acid. Here we report the development of an advanced procedure for preparation of the target amino acid via two-step SN2 and SN2′ alkylation of novel axially chiral nucleophilic glycine equivalent. Excellent yields and diastereoselectivity coupled with reliable and easy scalability render this method of immediate use for practical synthesis of (1R,2S)-vinyl-ACCA.

Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by sequential SN2-SN2′ dialkylation of (R)-N-(benzyl)proline-derived glycine Schiff base Ni(ii) complex

This work describes a new process for the asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid of high pharmaceutical importance. The sequence of the reactions includes PTC alkylation (SN2), homogeneous SN2′ cyclization followed by disassembly of the resultant Ni(ii) complex. All reactions are conducted under operationally convenient conditions and suitably scaled up to 6 g of the starting Ni(ii) complex. This journal is

Inhibitors of Serine Proteases

The present invention relates to compounds that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease. As such, they act by interfering with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The invention further relates to compositions comprising these compounds either for ex vivo use or for administration to a patient suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a patient by administering a composition comprising a compound of this invention.

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.

INHIBITORS OF SERINE PROTEASES FOR THE TREATMENT OF HCV INFECTIONS

The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt thereof. These compounds inhibit serine protease, particularly the hepatitis C virus NS3-NS4A protease.

INHIBITORS OF SERINE PROTEASES

The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt or mixtures thereof that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease.

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.

Enzymatic resolution of 1-amino-2-vinylcyclopropyl caboxylic acid methyl ester

An enantiomeric-resolving process for obtaining (1R,2S)-1-amino-2-vinylcyclopropyl carboxylic acid methyl ester by use of an esterase, and especially Alcalase?, is disclosed.

Enantioselective synthesis of (1R,2S) and (1S,2S) dehydrocoronamic acids

Thanks to the successive use of two esterases with different regioselectivities and conventional organic chemistry we have synthesized (1R,2S) and (1S,2S) dehydrocoronamic acids.