211618-76-7

Basic information

• Product Name: (S)-4-benzyl-2-azetidinone
• Synonyms: (S)-4-benzyl-2-azetidinone
• CAS NO: 211618-76-7
• Molecular Weight: 161.203
• Mol File: 211618-76-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-4-benzyl-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-benzyl-2-azetidinone(211618-76-7)
• EPA Substance Registry System: (S)-4-benzyl-2-azetidinone(211618-76-7)

Safety Data

• Hazardous Substances Data: 211618-76-7(Hazardous Substances Data)

Upstream product

• 15099-85-1 β-homo-(S)-phenylalanine 
• 211618-75-6 3(S)-{{(benzyloxy)carbonyl}amino}-4-phenylbutyric acid benzyl ester 
• 41518-17-6 Z-Phe-O-COO-isoBu 
• 15196-02-8 (S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone 
• 1161-13-3 N-Cbz-L-Phe 
• 777885-07-1 (+/-)-4-benzyl-2-azetidinone 
• 884344-36-9 (S)-4-benzyl-1-hydroxymethylazetidin-2-one 

Downstream Products

• 211618-78-9 (S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-azetidin-2-one 
• 15099-85-1 β-homo-(S)-phenylalanine 
• 211619-01-1 (2S,3R)-2-Benzyl-3-methyl-4-oxo-azetidine-1-carboxylic acid (pyridin-4-ylmethyl)-amide 
• 211619-02-2 (2S,3S)-2-Benzyl-3-methyl-4-oxo-azetidine-1-carboxylic acid (pyridin-4-ylmethyl)-amide 
• 211618-81-4 (3R,4S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-3-methyl-azetidin-2-one 
• 211618-79-0 (3S,4S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-3-methyl-azetidin-2-one 
• 211618-80-3 4(S)-benzyl-3(S)-methylazetidin-2-one 

Relevant articles and documents

Candida antarctica lipase B-catalyzed ring opening of 4-arylalkyl-substituted β-lactams

The Lipolase-catalyzed ring opening of racemic 4-benzyl- 3 and 4-phenylethyl-2-azetidinone 4 was performed with 0.5 equiv of H2O in diisopropyl ether at 45 °C. The resulting (S)-β-amino acid 5 or 6 (ee ≥ 87%) and (R)-β-lactam 7 or 8 (ee >99%) enantiomers could easily be separated. The ring opening of enantiomeric β-lactams with 18% aqueous HCl afforded the corresponding enantiopure β-amino acid hydrochlorides 9 and 10 (ee >99%).

Azetidinone derivatives for the treatment of HCMV infections

A compound of formula I wherein R1is hydrogen, methyl, ethyl, methoxy or methylthio; R2and R3each independently is hydrogen or lower alkyl; R4is hydrogen, lower alkyl, methoxy, ethoxy or benzyloxy; R5is lower alkyl, lower cycloalkyl, (CH2)mC(O)OR6wherein m is the integer 1 or 2 and R6is lower alkyl, phenyl optionally substituted; optionally Het or Het(lower alkyl); or R4and R5together with the nitrogen atom to which they are attached form a nitrogen containing ring optionally substituted with C(O)O-benzyl or with phenyl optionally substituted with C(O)OR7wherein R7is lower alkyl or (lower alkyl)phenyl; and Z is lower alkyl or optionally substituted phenyl or Het; with the proviso that when Z is (CH2)p-(Het), then R2and R3each is hydrogen; or a therapeutically acceptable acid addition salt thereof which compound is useful in the treatment of HCMV infections.