348620-02-0

Basic information

• Product Name: methyl N-benzyl-N-(2-buten-1-yl)carbamate
• Synonyms: methyl N-benzyl-N-(2-buten-1-yl)carbamate
• CAS NO: 348620-02-0
• Molecular Weight: 219.283
• Mol File: 348620-02-0.mol

Chemical Properties

• CAS DataBase Reference: methyl N-benzyl-N-(2-buten-1-yl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl N-benzyl-N-(2-buten-1-yl)carbamate(348620-02-0)
• EPA Substance Registry System: methyl N-benzyl-N-(2-buten-1-yl)carbamate(348620-02-0)

Safety Data

• Hazardous Substances Data: 348620-02-0(Hazardous Substances Data)

Upstream product

• 4784-77-4 (E/Z)-crotyl bromide 
• 5817-70-9 methyl N-benzylcarbamate 
• 100-46-9 benzylamine 

Downstream Products

• 348620-15-5 methyl N-crotyl-N-benzylmalonylamide 
• 136784-14-0 diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-benzylpyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate 
• 348620-51-9 2-amino-4-oxo-5-vinyl-7-benzyl-3,4,5,6-tetrahydropyrrolo[2,3-d]pyrimidine 
• 348620-33-7 1-benzyl-3-(methoxycarbonyl)-4-vinylpyrrolidin-2-one 
• 4393-07-1 N-crotylbenzylcarbamate 

Relevant articles and documents

A new route to 7-substituted derivatives of N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl) -ethyl]benzoyl}-L-glutamic acid [ALIMTA (LY231514, MTA)]

Alkylation of various primary amines with crotyl bromide, followed by DMAP-promoted acylation with methyl malonyl chloride to 4 and then manganic triacetate dihydrate/cupric acetate induced radical cyclization, gave 1-substituted-4-vinyl-3-carbomethoxy-2-pyrrolidinones (5). Thiation to the thiolactams 6 and guanidine cyclization then gave a series of 2-amino-3,4-dihydro-4-oxo-5-vinyl-7-substituted pyrrolo[2,3-d]pyrimidines (7). Palladium-catalyzed C-C coupling with diethyl 4-iodobenzoylglutamate led in one step via an unexpected redox reaction to the diethyl esters 9 of a series of 7-substituted derivatives of ALIMTA (LY231514, MTA), from which the target analogues 10 were readily prepared by saponification. Attempted deprotection at position 7 was successful in only one case (9d, R = CH2C6H3(OMe)2 (-3′,4′), which resulted in a known pentultimate precursor (9, R = H) of ALIMTA. The 7-substituted derivatives 10 proved to be inactive in vitro as inhibitors of cell division.