267244-45-1

Basic information

• Product Name: (2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine
• Synonyms: (2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine
• CAS NO: 267244-45-1
• Molecular Weight: 510.425
• Mol File: 267244-45-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine(267244-45-1)
• EPA Substance Registry System: (2S,3S,4S)-N-benzoyl-4-(bromoacetyl)-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine(267244-45-1)

Safety Data

• Hazardous Substances Data: 267244-45-1(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 267244-43-9 (2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-isopropylidenylpyrrolidine 
• 1028273-72-4 1-benzoyl-3-tert-butoxycarbonylmethyl-4-(1-trimethylsilanyloxy-vinyl)-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 267244-44-0 (2S,3S,4S)-acetyl-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-pyrrolidine 

Downstream Products

• 267244-49-5 (2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(2'-(methylamino)thiazol-4'-yl)pyrrolidine 
• 267244-48-4 (2S,3S,4S)-4-(2'-aminothiazol-4'-yl)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethylpyrrolidine 
• 267244-47-3 (2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(2'-phenylthiazol-4'-yl)pyrrolidine 
• 339557-52-7 (2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(quinoxal-2'-yl)pyrrolidine 
• 339557-55-0 (2S,3S,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(quinoxal-2'-yl)pyrrolidine 
• 342651-94-9 1-benzoyl-3-tert-butoxycarbonylmethyl-4-(3,4-dihydro-quinoxalin-2-yl)-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 342651-91-6 (2S,3S,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(2'-phenylimidazol-4'-yl)pyrrolidine 
• 342651-92-7 (2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(imidazo[1',2'-a]pyrid-2'-yl)pyrrolidine 
• 267244-46-2 (2S,3S,4S)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(2'-methylthiazol-4'-yl)pyrrolidine 

Relevant articles and documents

Parallel synthesis of novel heteroaromatic acromelic acid analogues from kainic acid

A range of new C-4 heteroaromatic acromelic acid analogues has been synthesized in a parallel fashion from (-)-α-kainic acid 1. Protection of the amine and carboxylate groups of 1 followed by ozonolysis gave methyl ketone 8. A silyl enol ether 9, generated regiospecifically from the methyl ketone 8 using "kinetic" conditions, was brominated in situ with phenyltrimethylammonium perbromide to give the key α-bromo ketone 10. Parallel cyclization reactions of bromo ketone 10 with thioamides and thioureas were then performed. The aromatic heterocyclic derivatives 11a-d and 19 produced were deprotected to give the new kainoid amino acids 6a-d and 25 in excellent yield. Compounds 6a and 6c show strong binding to the kainate receptor. Reaction of 10 with alternative condensing agents was also briefly investigated.