1000388-05-5

Basic information

• Product Name: 1-(4-methoxybenzyl)-3,3-difluoro-4-(pyridin-4-yl)azetidin-2-one
• Synonyms: 1-(4-methoxybenzyl)-3,3-difluoro-4-(pyridin-4-yl)azetidin-2-one
• CAS NO: 1000388-05-5
• Molecular Weight: 304.296
• Mol File: 1000388-05-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-(4-methoxybenzyl)-3,3-difluoro-4-(pyridin-4-yl)azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-methoxybenzyl)-3,3-difluoro-4-(pyridin-4-yl)azetidin-2-one(1000388-05-5)
• EPA Substance Registry System: 1-(4-methoxybenzyl)-3,3-difluoro-4-(pyridin-4-yl)azetidin-2-one(1000388-05-5)

Safety Data

• Hazardous Substances Data: 1000388-05-5(Hazardous Substances Data)

Upstream product

• 872-85-5 pyridine-4-carbaldehyde 
• 1075221-29-2 C₁₄H₁₄N₂O 
• 667-27-6 Ethyl bromodifluoroacetate 
• 2393-23-9 4-methoxy-benzylamine 
• 1000387-95-0 C₁₄H₁₄N₂O 

Relevant articles and documents

Regio- and stereoselective lipase-catalysed acylation of methyl α-D-glycopyranosides with fluorinated β-lactams

Burkholderia cepacia lipase (lipase PS-D) catalysed acylation with 3,3-difluoro-4-phenyl-, -thiophen-3-yl- and -4-pyridylazetidin-2-ones was examined for the formation of N-Boc-protected 6-O-acylated sugar-β-amino acid conjugates from methyl α-D-galacto-, -gluco- and mannopyranosides and Boc2O. The 6-O-acylated glycopyranoside-β-amino acid conjugates were isolated and characterized. The low solubility of the gluco- and mannopyranosides and the high reactivity of the pyridylazetidinone restricted product formation. Activation of the β-lactam ring by the presence of fluorine substituents was shown to be necessary for the enzymatic acylation reaction. The (S)-enantiomers of the racemic β-lactam substrates reacted with the sugars. The lipase-catalysed diastereoselective ring-opening of aromatic and hetero-aromatic β-lactams was explored for the formation of β-amino acid conjugates of methyl α-D-glycopyranosides. Potential hydrolytic side-reactions were minimized by a suitable choice of solvent, lipase preparation and the use of molecular sieves.

Chemoselective and stereoselective synthesis of gem-difluoro-β-aminoesters or gem-difluoro-β-lactams from ethylbromodifluoroacetate and imines during Reformatsky reaction

The chemoselective and stereoselective synthesis of gem-difluoro-β-aminoesters or gem-difluoro-β-lactams was investigated from ethylbromodifluoroacetate and imines during Reformatsky reaction. Influence of various reaction parameters, such as nature of the amine part, nature of the chiral auxiliary, was evaluated. High levels of stereoselectivity (up to 98%) were obtained for gem-difluoro-β-aminoesters and gem-difluoro-β-lactams using either (R)-phenylglycinol or (R)-methoxyphenylglycinol.