476312-66-0

Basic information

• Product Name: [3-(3-bromo-3-phenyl-propionylamino)-propyl]-carbamic acid tert-butyl ester
• Synonyms: [3-(3-bromo-3-phenyl-propionylamino)-propyl]-carbamic acid tert-butyl ester
• CAS NO: 476312-66-0
• Molecular Weight: 385.301
• Mol File: 476312-66-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [3-(3-bromo-3-phenyl-propionylamino)-propyl]-carbamic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [3-(3-bromo-3-phenyl-propionylamino)-propyl]-carbamic acid tert-butyl ester(476312-66-0)
• EPA Substance Registry System: [3-(3-bromo-3-phenyl-propionylamino)-propyl]-carbamic acid tert-butyl ester(476312-66-0)

Safety Data

• Hazardous Substances Data: 476312-66-0(Hazardous Substances Data)

Upstream product

• 15463-91-9 3-bromo-3-phenylpropionic acid 
• 75178-96-0 N-Boc-1,3-diaminopropane 

Downstream Products

• 88909-10-8 (R,S)-4-phenyl-1,5-diazacyclooctan-2-one 
• 89044-85-9 N-(3-aminopropyl)-4-phenylazetidin-2-one 
• 476312-67-1 [3-(2-oxo-4-phenylazetidin-1-yl)propyl]carbamic acid tert-butyl ester 

Relevant articles and documents

β-lactams as building blocks in the synthesis of macrocyclic spermine and spermidine alkaloids

Syntheses of the macrocyclic spermidine alkaloids (±)-celacinnine (1) and (±)-dihydroperiphylline (2) as well as the related spermine alkaloid (±)-verbascenine (3) were accomplished by means of sequential ring expansions of smaller lactam rings. Three ring expansion methods were employed: (1) transamidation of N-(aminoalkyl)lactams, (2) β-lactam-lactim ether condensation followed by reductive cleavage of the bicyclic 4-oxotetrahydropyrimidine product with NaBH3CN/AcOH and (3) bicyclic acyl hydrazine formation followed by N-N bond cleavage with Na/NH3. Each synthesis features ring expansion of a 4-phenylazetidin-2-one intermediate that undergoes transamidative ring expansion or lactim ether condensation.