252681-03-1

Basic information

• Product Name: (4S)-3,3-difluoro-1-((1R)-2-hydroxy-1-phenylethyl)-4-phenylazetidin-2-one
• Synonyms: (4S)-3,3-difluoro-1-((1R)-2-hydroxy-1-phenylethyl)-4-phenylazetidin-2-one
• CAS NO: 252681-03-1
• Molecular Weight: 303.308
• Mol File: 252681-03-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (4S)-3,3-difluoro-1-((1R)-2-hydroxy-1-phenylethyl)-4-phenylazetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-3,3-difluoro-1-((1R)-2-hydroxy-1-phenylethyl)-4-phenylazetidin-2-one(252681-03-1)
• EPA Substance Registry System: (4S)-3,3-difluoro-1-((1R)-2-hydroxy-1-phenylethyl)-4-phenylazetidin-2-one(252681-03-1)

Safety Data

• Hazardous Substances Data: 252681-03-1(Hazardous Substances Data)

Upstream product

• 667-27-6 Ethyl bromodifluoroacetate 
• 153924-63-1 β-[(phenylmethylene)amino]-[R-(E)-]-benzeneethanol 
• 249920-08-9 2,4-diphenyl-1,3-oxazolidine 
• 109522-62-5 (2-ethoxy-1,1-difluoro-2-oxoethyl)zinc(II) bromide 

Downstream Products

• 667938-19-4 (2-{Benzyl-[(S)-2,2-difluoro-3-((R)-2-hydroxy-1-phenyl-ethylamino)-3-phenyl-propionyl]-amino}-2-phenyl-acetylamino)-acetic acid ethyl ester 
• 252681-18-8 (3S)-3-amino-2,2-difluoro-3-phenylpropanoic acid hydrochloride 
• 252681-06-4 (4S)-3,3-difluoro-4-phenyl-1-(1-phenylvinyl)azetidin-2-one 
• 252681-07-5 (4S)-3,3-difluoro-4-phenylazetidin-2-one 
• 252681-04-2 (3S)-2,2-difluoro-3-((1R)-2-hydroxy-1-phenylethylamino)-3-phenylpropanoic acid 

Relevant articles and documents

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.

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.