252681-07-5

Basic information

• Product Name: (4S)-3,3-difluoro-4-phenylazetidin-2-one
• Synonyms: (4S)-3,3-difluoro-4-phenylazetidin-2-one
• CAS NO: 252681-07-5
• Molecular Weight: 183.157
• Mol File: 252681-07-5.mol

Chemical Properties

• CAS DataBase Reference: (4S)-3,3-difluoro-4-phenylazetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-3,3-difluoro-4-phenylazetidin-2-one(252681-07-5)
• EPA Substance Registry System: (4S)-3,3-difluoro-4-phenylazetidin-2-one(252681-07-5)

Safety Data

• Hazardous Substances Data: 252681-07-5(Hazardous Substances Data)

Upstream product

• 252681-06-4 (4S)-3,3-difluoro-4-phenyl-1-(1-phenylvinyl)azetidin-2-one 
• 623-42-7 butanoic acid methyl ester 
• 252681-09-7 rac-3,3-difluoro-4-phenylazetidin-2-one 
• 109-21-7 butyl butyrate 
• 249920-08-9 2,4-diphenyl-1,3-oxazolidine 
• 252681-03-1 (4S)-3,3-difluoro-1-((1R)-2-hydroxy-1-phenylethyl)-4-phenylazetidin-2-one 
• 1037299-25-4 Trifluoro-methanesulfonic acid (R)-2-((S)-3,3-difluoro-2-oxo-4-phenyl-azetidin-1-yl)-2-phenyl-ethyl ester 
• 1037299-22-1 C₁₇H₁₅F₂NO₂ 
• 78-81-9 isobutylamine 
• 75-31-0 isopropylamine 
• 109-73-9 N-butylamine 
• 1277191-97-5 (S)-tert-butyl N-(2,2-difluoro-3-oxo-1,3-diphenylpropyl)carbamate 
• 1277192-13-8 (S)-tert-butyl N-(2-(phenoxycarbonyl)-2,2-difluoro-1-phenylethyl)carbamate 
• 150884-50-7 benzaldehyde N-boc imine 

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.

Chiral phosphoric acid catalyzed enantioselective synthesis of β-amino-α,α-difluoro carbonyl compounds

A biphenol-based chiral phosphoric acid bearing a 9-anthryl group at each of the 3,3′-positions catalyzed the asymmetric Mannich-type reaction of N-Boc imine with difluoroenol silyl ethers in the presence of MS3A in THF to afford β-amino-α,α-difluoroketon

Burkholderia cepacia lipase and activated β-lactams in β-dipeptide and β-amino amide synthesis

The work describes fluorine-activated and N-Boc-activated β-lactams as acyl donors to N-nucleophiles in the presence of Burkholderia cepacia lipase (lipase PS-D). Fluorine activation at the β-lactam ring causes the ring to open in high enantioselectivity

Rhodium-catalyzed Reformatsky-type reaction for asymmetric synthesis of difluoro-β-lactams using menthyl group as a chiral auxiliary

We developed a new methodology for the asymmetric Reformatsky-type reaction of (-)-menthyl bromodifluoroacetate (2) with imine in the presence of RhCl(PPh3)3. Ester 2 with the cost-effective chiral auxiliary gave (S)-difluoro-β-lacta

Enantioselective acylation of alcohols with fluorinated β-phenyl-β-lactams in the presence of Burkholderia cepacia lipase

This paper concentrates on studies of the acylation of alcohols with 3,3-difluoro-4-phenylazetidin-2-one rac-1, trans-3-fluoro-4-phenylazetidin-2-one rac-2 and 4-phenylazetidin-2-one rac-3 in the presence of immobilized lipase PS from Burkholderia cepacia in dry tert-butyl methyl ether (TBME). Fluorine activation in the compounds studied was essential in order to split the β-lactam ring with lipase PS. The highly enantioselective ring opening of rac-1 and rac-2 with methanol (1-butanol was also studied) allowed the preparation of the (R/(3R,4R))-β-lactams as the unreacted enantiomers and (S/(2S,3S))-β-amino esters as the product enantiomers with an ee >99%. Under the same conditions, rac-3 was totally unreactive. The possibility for a competing hydrolysis caused by water in the enzyme preparations is also discussed.

Chemoenzymatic preparation of fluorine-substituted β-lactam enantiomers exploiting Burkholderia cepacia lipase

Both enantiomers of fluorinated and non-fluorinated 4-phenyl-2-azetidinones are prepared in high enantiopurities (ee 99%) by a chemoenzymatic method, using a double resolution technique to N-hydroxymethylated β-lactams in the presence of Burkholderia cepa

Enantioselective synthesis of α,α-difluoro-β-amino acid and 3,3- difluoroazetidin-2-one via the reformatsky-type reaction of ethyl bromodifluoroacetate with chiral 1,3-oxazolidines

Chiral oxazolidines 2a-e can be diastereoselectively alkylated with BrCF2CO2Et to furnish 3,3-difluoroazetidin-2-ones 3a-e with up to 99% de. Selective cleavage of the chiral appendage provided the corresponding unsubstituted azetidinones. Formation of optically pure α,α-difluoro-β- amino acids 5a-c can be achieved by acidic hydrolysis of N-vinyl-azetidin-2- ones.