102284-41-3

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 2-(chloroacetyl)-, 1,1-dimethylethyl ester, (2S)-
• CAS NO: 102284-41-3
• Molecular Formula: C11H18ClNO3
• Molecular Weight: 247.722
• Mol File: 102284-41-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 2-(chloroacetyl)-, 1,1-dimethylethyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 2-(chloroacetyl)-, 1,1-dimethylethyl ester, (2S)-(102284-41-3)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 2-(chloroacetyl)-, 1,1-dimethylethyl ester, (2S)-(102284-41-3)

Safety Data

• Hazardous Substances Data: 102284-41-3(Hazardous Substances Data)

Usage

Chemical compound

1-Pyrrolidinecarboxylic acid, 2-(chloroacetyl)-, 1,1-dimethylethyl ester, (2S)-

Appearance

White to off-white crystalline solid

Molecular weight

273.76 g/mol

Solubility

Insoluble in water, soluble in organic solvents such as methanol and ethanol

Stereochemistry

Chiral molecule with a single stereocenter, indicated by the (2S)in its name, meaning it can exist in two enantiomeric forms

Use

Often used in peptide synthesis as a protecting group, and has various applications in organic synthesis and pharmaceutical research, particularly in the development of peptide-based drugs and pharmaceuticals.

Upstream product

• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 3926-62-3 sodium monochloroacetic acid 
• 593-71-5 Chloroiodomethane 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 101130-03-4 tert-butyl (S)-2-(diazoacetyl)pyrrolidine-1-carboxylate 
• 186581-53-3 diazomethane 

Downstream Products

• 102284-44-6 phenyl N-<(N-boc-L-prolyl)methyl>-N-isopropylcarbamate 
• 102284-47-9 S-benzyl N-<(N-boc-L-prolyl)methyl>-N-isopropylthiocarbamate 
• 102284-50-4 N-<(N-boc-L-prolyl)methyl>-N-isopropyl-N'-(p-nitrophenyl)urea 
• 102284-43-5 p-nitrophenyl N-<(N-boc-L-prolyl)methyl>-N-isopropylcarbamate 
• 102284-49-1 S-1-phenyl-5-tetrazolyl N-<(N-boc-L-prolyl)methyl>-N-isopropylthiocarbamate 
• 102284-45-7 pentafluorophenyl N-<(N-boc-L-prolyl)methyl>-N-isopropylcarbamate 
• 102284-52-6 phenyl N-(L-prolylmethyl)-N-isopropylcarbamate hydrochloride 
• 102284-54-8 S-benzyl N-(L-prolylmethyl)-N-isopropylcarbamate hydrochloride 
• 102284-51-5 p-nitrophenyl N-(L-prolylmethyl)-N-isopropylcarbamate hydrochloride 
• 102284-57-1 N-(L-prolylmethyl)-N-isopropyl-N'-(p-nitrophenyl)urea hydrochloride 
• 92279-33-9 phenyl N-<(methoxysuccinyl)-L-alanyl-L-alanyl-L-prolylmethyl>-N-isopropylcarbamate 
• 102284-59-3 S-benzyl N-<(methoxysuccinyl)-L-alanyl-L-alanyl-L-prolylmethyl>-N-isopropylcarbamate 
• 102284-56-0 S-1-phenyl-5-tetrazolyl N-(L-prolylmethyl)-N-isopropylcarbamate hydrochloride 
• 102284-53-7 pentafluorophenyl N-(L-prolylmethyl)-N-isopropylcarbamate hydrochloride 

Relevant articles and documents

Efficient and Scalable Synthesis of Glucokinase Activator with a Chiral Thiophenyl-Pyrrolidine Scaffold

Herein we describe the practical synthesis of a potent glucokinase activator (1) that has a chiral thiophenyl-pyrrolidine scaffold. The key to the successful synthesis was the application of a telescoped chiral-pool synthesis from a commercially available l-proline methyl ester derivative to introduce the chirality of the thiophenyl-pyrrolidine moiety. This second-generation synthesis of 1 provided several advantages over the previous method including an operational simplicity and avoidance of purification by column chromatography. The industrial relevance of this synthetic method in large-scale preparation was demonstrated by the production of 54.6 kg of 1 with an excellent chemical and optical purity.

Extended structure-activity relationship and pharmacokinetic investigation of (4-quinolinoyl)glycyl-2-cyanopyrrolidine inhibitors of fibroblast activation protein (FAP)

Fibroblast activation protein (FAP) is a serine protease related to dipeptidyl peptidase IV (DPPIV). It has been convincingly linked to multiple disease states involving remodeling of the extracellular matrix. FAP inhibition is investigated as a therapeutic option for several of these diseases, with most attention so far devoted to oncology applications. We previously discovered the N-4-quinolinoyl-Gly-(2S)-cyanoPro scaffold as a possible entry to highly potent and selective FAP inhibitors. In the present study, we explore in detail the structure-activity relationship around this core scaffold. We report extensively optimized compounds that display low nanomolar inhibitory potency and high selectivity against the related dipeptidyl peptidases (DPPs) DPPIV, DPP9, DPPII, and prolyl oligopeptidase (PREP) the log D values, plasma stabilities, and microsomal stabilities of selected compounds were found to be highly satisfactory. Pharmacokinetic evaluation in mice of selected inhibitors demonstrated high oral bioavailability, plasma half-life, and the potential to selectively and completely inhibit FAP in vivo.

A practical method for the preparation of α'-chloroketones of N-carbanaate protected-α-aminoacids

A practical method for the preparation of α-N-BOC-epoxides from protected amino acid esters based on the Kowalski homologation reaction is described. This procedure can be readily performed on a large scale without the use of hazardous reagents and has allowed preparation of epoxides 3 in multi-kilogram quantities.