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
• Article Data: 12

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

General Description

Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate is a chemical compound commonly used in organic synthesis and medicinal chemistry. It is a derivative of the amino acid proline, and is often employed as a chiral building block in the synthesis of pharmaceuticals and biologically active molecules. The Boc (tert-butoxycarbonyl) protecting group helps to prevent unwanted reactions at specific sites on the molecule, while the benzyl group provides stability and solubility. Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate is a versatile intermediate that can be utilized in the preparation of a wide range of pharmaceutical and agrochemical products.

Upstream product

• 100-39-0 benzyl bromide 
• 84348-37-8 N-tert-butoxycarbonyl-4-oxo-L-proline 
• 89813-47-8 N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 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 

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.

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

Fluorinated proline derivatives have found diverse applications in areas ranging from medicinal chemistry over structural biochemistry to organocatalysis. Depending on the stereochemistry of monofluorination at the proline 3- or 4-position, different effe

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.