154456-97-0

Basic information

• Product Name: Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate
• Synonyms: Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate;2-benzyl 1-(tert-butyl) 4-oxopyrrolidine-1,2-dicarboxylate;(S)-4-Oxopyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester;N-(tert-butyloxycarbonyl)-4-oxoproline benzyl ester;(S)-2-benzyl1-tert-butyl4-oxopyrrolidine-1,2-dicarboxylate(WXC07842)
• CAS NO: 154456-97-0
• Molecular Formula: C₁₇H₂₁NO₅
• Molecular Weight: 319.36
• Mol File: 154456-97-0.mol

Chemical Properties

• Boiling Point: 439.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.219±0.06 g/cm3(Predicted)
• PKA: -3.90±0.40(Predicted)
• CAS DataBase Reference: Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate(154456-97-0)
• EPA Substance Registry System: Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate(154456-97-0)

Safety Data

• Hazardous Substances Data: 154456-97-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate is used as a chiral building block for the synthesis of pharmaceuticals and biologically active molecules. Its unique structure and protecting group make it a valuable component in the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate is also used as an intermediate in the synthesis of agrochemical products. Its versatility allows it to be incorporated into the development of various agrochemicals, contributing to advancements in agriculture and pest control.

Upstream product

• 89813-47-8 N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 144-55-8 sodium hydrogencarbonate 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 51-35-4 4R-4-hydroxyproline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 100-39-0 benzyl bromide 
• 84348-37-8 N-tert-butoxycarbonyl-4-oxo-L-proline 

Downstream Products

• 84348-37-8 N-tert-butoxycarbonyl-4-oxo-L-proline 
• 249581-21-3 (1R,3R,5R,7S)-3-Benzoyl-8-oxo-6-aza-bicyclo[3.2.1]octane-6,7-dicarboxylic acid 7-benzyl ester 6-tert-butyl ester 
• 474417-78-2 benzyl (2S)-N-tert-butoxycarbonyl-4-difluoromethyleneprolinate 
• 470482-41-8 (2S,4S)-1-[(tert-butoxy)carbonyl]-4-(trifluoromethyl)pyrrolidine-2-carboxylic acid 
• 474417-79-3 (2S,4S)-N-tert-butoxycarbonyl-4-difluoromethylproline 
• 474417-77-1 2-benzyl 1-(tert-butyl) (S)-4-(trifluoromethyl)-2.5-dihydro-1H-pyrrole-1.2-dicarboxylate 
• 474417-76-0 benzyl (2S,4S)-N-tert-butoxycarbonyl-4-hydroxy-4-trifluoromethylprolinate 
• 898275-40-6 2-benzyl 1-tert-butyl (2S)-4-(2-methoxy-2-oxoethylidene)-1,2-pyrrolidinedicarboxylate 
• 1283146-43-9 (2S,4S)-1-(tert-butoxycarbonyl)-4-ethylpyrrolidine-2-carboxylic acid 
• 1283147-26-1 (S)-2-benzyl 1-tert-butyl 4-ethylidenepyrrolidine-1,2-dicarboxylate 

Relevant articles and documents

A Novel Entry to Carbenoid Species via β-Ketosulfoxonium Ylides

In the presence of suitable rhodium(II) catalysts, lactam derived β-ketosulfoxonium ylides can be transformed to β-oxonitrogen heterocycles, e. g. substituted 4-oxopyrrolidine, via intermediates of carbenoid nature.

Tetrahydropyridopyrimidine compound with anti-tumor activity

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Synthesis and Conformational Properties of 3,4-Difluoro- l -prolines

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Discovery of Pyrrolidine-Containing GPR40 Agonists: Stereochemistry Effects a Change in Binding Mode

A novel series of pyrrolidine-containing GPR40 agonists is described as a potential treatment for type 2 diabetes. The initial pyrrolidine hit was modified by moving the position of the carboxylic acid, a key pharmacophore for GPR40. Addition of a 4-cis-CF3 to the pyrrolidine improves the human GPR40 binding Ki and agonist efficacy. After further optimization, the discovery of a minor enantiomeric impurity with agonist activity led to the finding that enantiomers (R,R)-68 and (S,S)-68 have differential effects on the radioligand used for the binding assay, with (R,R)-68 potentiating the radioligand and (S,S)-68 displacing the radioligand. Compound (R,R)-68 activates both Gq-coupled intracellular Ca2+ flux and Gs-coupled cAMP accumulation. This signaling bias results in a dual mechanism of action for compound (R,R)-68, demonstrating glucose-dependent insulin and GLP-1 secretion in vitro. In vivo, compound (R,R)-68 significantly lowers plasma glucose levels in mice during an oral glucose challenge, encouraging further development of the series.

ARYL, HETEROARYL, AND HETEROCYCLIC COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS

Compounds, methods of use, and processes for making inhibitors of complement Factor D comprising Formula I, or a pharmaceutically acceptable salt or composition thereof wherein R12 or R13 on the A group is an aryl, heteroaryl or heterocycle (R32) are provided. The inhibitors of Factor D described herein reduce the excessive activation of complement.

PROLINE DERIVATIVES AND USE THEREOF AS DRUGS

The present invention aims at providing compounds having therapeutic effects due to a DPP-IV inhibitory action, and satisfactory as pharmaceutical products. The present inventors have found that derivatives having a substituent introduced into the γ-position of proline represented by the formula (I) wherein each symbol is as defined in the specification, have a potent DPP-IV inhibitory activity, and completed the present invention by increasing the stability.

Practical synthesis of Boc-protected cis-4-trifluoromethyl and cis-4-difluoromethyl-L- prolines

A short, efficient, and diastereomerically pure synthesis of N-Boc-cis-4-trifluoromethyl-L-proline (7) and N-Boc-cis-4-difluoromethyl-L-proline (9) from N-Boc-4-oxo- L-proline (4) is described. The reaction of 4 with Me3SiCF3 and the conversion of the carbonyl group of 4 into the difluoromethylene group are the key steps for the synthesis of 7 and 9, respectively.

Stereoselective synthesis of novel chimerical amino acids via a photochemical key step

The synthesis of novel chimerical amino acid derivatives 6-8 bearing the 6-azatricyclo[3.3.1.033,7]nonane (methanotropane) skeleton is described. Starting with one chirality centre in L-4-oxoprolines 2 we succeeded in the fully stereoselective introduction of four new chirality centres. The key step of our synthetic route is a photochemical cyclization of phenyl ketones, whose stereoselectivity has been explained by the different stability of the triplet biradical conformers.

Synthesis of kainoid analogues

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