182866-68-8

Basic information

• Product Name: (S)-2-(1-Methoxycarbonyl-2-oxo-propylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester
• CAS NO: 182866-68-8
• Molecular Weight: 362.382
• Mol File: 182866-68-8.mol

Chemical Properties

• CAS DataBase Reference: (S)-2-(1-Methoxycarbonyl-2-oxo-propylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(1-Methoxycarbonyl-2-oxo-propylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester(182866-68-8)
• EPA Substance Registry System: (S)-2-(1-Methoxycarbonyl-2-oxo-propylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester(182866-68-8)

Safety Data

• Hazardous Substances Data: 182866-68-8(Hazardous Substances Data)

Upstream product

• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 24762-04-7 2-Diazo-3-oxo-butyric acid methyl ester 
• 34079-31-7 Z-Pro-NH₂ 

Downstream Products

• 203782-31-4 (S)-2-[4-(1-Methoxycarbonyl-2-oxo-propylcarbamoyl)-5-methyl-oxazol-2-yl]-pyrrolidine-1-carboxylic acid benzyl ester 
• 203782-27-8 (S)-2-(1-benzyloxycarbonyltetrahydropyrrol-2-yl)-5-methyloxazole-4-carboxylic acid 
• 203782-29-0 (S)-2-(1-benzyloxycarbonyltetrahydropyrrol-2-yl)-5-methyloxazole-4-carboxamide 

Relevant articles and documents

Synthesis of functionalised oxazoles and bis-oxazoles

A new method for the synthesis of oxazoles, and in particular chiral non-racemic oxazoles derived from amino acids, has been developed. Thus, rhodium(II) catalysed reaction of diazocarbonyl compounds 6 and 11 in the presence of amides 8 and 10 results in regioselective insertion of the carbenoid into the amide N-H bond with formation of the β-carbonyl amides 9 and 12. Cyclodehydration of amides 9 and 12 using triphenylphosphine-iodine-triethylamine gives functionalised oxazoles 7 and 13. The oxazoles 13c and 13f were converted into the bis-oxazoles 17a and 17b by a second rhodium(II) catalysed regioselective N-H insertion reaction on the amides 15, followed by cyclodehydration.