194594-24-6

Basic information

• Product Name: 1,2-Pyrrolidinedicarboxylic acid, 5-Methoxy-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)-
• Synonyms: 1,2-Pyrrolidinedicarboxylic acid, 5-Methoxy-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)-;(2S)-1-tert-Butyl 2-ethyl 5-methoxypyrrolidine- 1,2-dicarboxylate;1-(tert-butyl) 2-ethyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate
• CAS NO: 194594-24-6
• Molecular Formula: C₁₃H₂₃NO₅
• Molecular Weight: 273.32542
• Mol File: 194594-24-6.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,2-Pyrrolidinedicarboxylic acid, 5-Methoxy-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Pyrrolidinedicarboxylic acid, 5-Methoxy-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)-(194594-24-6)
• EPA Substance Registry System: 1,2-Pyrrolidinedicarboxylic acid, 5-Methoxy-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)-(194594-24-6)

Safety Data

• Hazardous Substances Data: 194594-24-6(Hazardous Substances Data)

Usage

General Description

1,2-Pyrrolidinedicarboxylic acid, 5-Methoxy-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)- is a chemical compound with a complex and lengthy name. It is an ester derivative of 5-methoxy-1,2-pyrrolidinedicarboxylic acid, with a (2S)- configuration. 1,2-Pyrrolidinedicarboxylic acid, 5-Methoxy-, 1-(1,1-diMethylethyl) 2-ethyl ester, (2S)- is important in organic synthesis and pharmaceutical research, as it has potential applications in drug development and chemical processes. Its specific properties and potential uses would depend on its structure and behavior in various chemical reactions.

Upstream product

• 67-56-1 methanol 
• 194594-23-5 5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 98-79-3 L-Pyroglutamic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 7149-65-7 ethyl (S)-pyroglutamate 

Downstream Products

• 676560-84-2 (2S,5S)-5-methylpyrrolidine-2-carboxylic acid ethyl ester 
• 166941-67-9 Ethyl (2S,5R)-5-methylprolinate 
• 158567-93-2 β-(S)-5-Ethoxycarbonyl-2-phenylpyrrolidine 
• 166941-66-8 α-(S)-5-Ethoxycarbonyl-2-phenylpyrrolidine 
• 214193-11-0 (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-formic acid ethyl ester 
• 214193-13-2 cis-4,5-methano-L-proline 
• 214193-12-1 (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-3 -carboxylic acid 
• 220724-82-3 (2S,5S)-5-[(Benzyloxycarbonyl-tert-butoxycarbonylmethyl-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 

Relevant articles and documents

Invention of MK-8262, a Cholesteryl Ester Transfer Protein (CETP) Inhibitor Backup to Anacetrapib with Best-in-Class Properties ()

Cholesteryl ester transfer protein (CETP) represents one of the key regulators of the homeostasis of lipid particles, including high-density lipoprotein (HDL) and low-density lipoprotein (LDL) particles. Epidemiological evidence correlates increased HDL and decreased LDL to coronary heart disease (CHD) risk reduction. This relationship is consistent with a clinical outcomes trial of a CETP inhibitor (anacetrapib) combined with standard of care (statin), which led to a 9% additional risk reduction compared to standard of care alone. We discuss here the discovery of MK-8262, a CETP inhibitor with the potential for being the best-in-class molecule. Novel in vitro and in vivo paradigms were integrated to drug discovery to guide optimization informed by a critical understanding of key clinical adverse effect profiles. We present preclinical and clinical evidence of MK-8262 safety and efficacy by means of HDL increase and LDL reduction as biomarkers for reduced CHD risk.

Trans-2,5-Disubstituted pyrrolidines: Rapid stereocontrolled access from sulfones

A direct method for the reliable synthesis of trans-2,5-distributed pyrrolidines from pyroglutamic acid that was conducted at scale and without chromatographic purification of key intermediates was investigated. An analogous reaction involving the partial reduction of succinimides and displacement of the resulting lactol with benzenesulfinic acid yields sulfonyl pyrrolidinones. It was found that a highly diastereoselective and general approach to 2,5-difunctionalized pyrrolidines could be achieved by applying this strategy to the pyroglutamate system. The four step synthesis required no chromatographic purification of intermediates, where the product sulfone was readily purified by recrystallization and the sequence proceeded in 52% overall yield. The results show that such an approach would be of great importance for the preparation of substituted pyrrolidines in natural product systems.

Design and synthesis of potent, non-peptide inhibitors of HCV NS3 protease

Starting from a hexapeptide boronic acid lead, 3-amino bicyclic pyrazinones as novel β-sheet dipeptide mimetics have been designed and synthesized. Side-chain manipulation of this scaffold generated a series of potent, nonpeptidic inhibitors of HCV NS3 protease.