114341-89-8

Basic information

• Product Name: 3-[(2R)-2-[(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxo-azetidin-2-yl]propanoyl]-4,4-dimethyl-oxazolidin-2-one
• Synonyms: 2-Oxazolidinone, 3-[(2R)-2-[(2R,3S)-3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-4-oxo-2-azetidinyl]-1-oxopropyl]-4,4-dimethyl-
• CAS NO: 114341-89-8
• Molecular Formula: C₁₉H₃₄N₂O₅Si
• Molecular Weight: 398.57
• EINECS: 601-306-2
• Mol File: 114341-89-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 510.8°C at 760 mmHg
• Flash Point: 262.7°C
• Density: 1.083g/cm³
• Vapor Pressure: 1.5E-10mmHg at 25°C
• Refractive Index: 1.482
• CAS DataBase Reference: 3-[(2R)-2-[(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxo-azetidin-2-yl]propanoyl]-4,4-dimethyl-oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(2R)-2-[(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxo-azetidin-2-yl]propanoyl]-4,4-dimethyl-oxazolidin-2-one(114341-89-8)
• EPA Substance Registry System: 3-[(2R)-2-[(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxo-azetidin-2-yl]propanoyl]-4,4-dimethyl-oxazolidin-2-one(114341-89-8)

Safety Data

• Hazardous Substances Data: 114341-89-8(Hazardous Substances Data)

Upstream product

• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 150968-18-6 4,4-dimethyl-3-propionyloxazolidin-2-one 
• 131991-76-9 (1S,3R,5R,6R)-8-aza-3-(benzyloxymethyl)-5-methyl-2,4-dioxa-bicyclo<4.2.0>octan-7-one 
• 127680-55-1 (1S,3R,5R,6R)-8-aza-3-acetyl-5-methyl-2,4-dioxa-bicyclo<4.2.0>octan-7-one 
• 130919-59-4 (1S,3R,5R,6R)-8-aza-3-<1-(S)-hydroxyethyl>-5-methyl-2,4-dioxa-bicyclo<4.2.0>octan-7-one 
• 131991-77-0 (1S,3R,5R,6R)-8-aza-3-(hydroxymethyl)-5-methyl-2,4-dioxa-bicyclo<4.2.0>octan-7-one 
• 130919-57-2 (1S,5R,6R)-8-aza-5-methyl-2,4-dioxa-bicyclo<4.2.0>octan-3,7-dione 
• 127680-56-2 (3R,4R)-4-acetoxy-3-<(R)-1-formyloxyethyl>-2-azetidinone 
• 127680-54-0 (1S,3R,5R,6R)-8-aza-3-<1-(S)-benzyloxyethyl>-5-methyl-2,4-dioxa-bicyclo<4.2.0>octan-7-one 
• 114341-88-7 3-(2'-bromopropionyl)-4,4-dimethyloxazolidin-2-one 
• 127680-58-4 (3S,4R)-3-<(R)-1-formyloxyethyl>-4-<(S)-1-(4,4-dimethyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 127759-84-6 (3S,4R)-3-<(R)-1-formyloxyethyl>-4-<(R)-1-(4,4-dimethyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 127680-58-4 (3S,4R)-3-<(R)-1-formyloxyethyl>-4-<(R,S)-1-(4,4-dimethyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 114341-91-2 (3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(R,S)-1-(4,4-dimethyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 

Downstream Products

• 93711-85-4 (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid 
• 96035-98-2 (3S,4S)-4-<(1R)-1-benzyloxycarbonylethyl>-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-2-azetidinone 

Relevant articles and documents

Process for the preparation of 4-substituted azetidinone derivatives

Disclosed is a process for the preparation of a 4-substituted azetidinone derivative, which comprises reacting an azetidinone derivative and an amide compound in the presence of a magnesium compound such as those represented by the following formulas (II): and (IV): represented by the following formula (III): MgR5R6??(III) wherein R5represents a C1-12alkyl group, a C2-5alkenyl group, a 5- to 8-membered alicyclic group which may be substituted by a lower C1-4alkyl group, a phenyl group which may be substituted by a lower C1-4alkyl group, a lower C1-4alkoxy group or a halogen atom or a benzyl group which may be substituted by a lower C1-4alkyl group, a lower C1-4alkoxy group or a halogen atom, and R6represents a halogen atom, a methanesulfonyloxy group, a benzenesulfonyloxy group, a p-toluenesulfonyloxy group, a trifluoromethanesulfonyloxy group, an acetoxy group which may be substituted by a halogen atom or a cyano group or an OR7group (R7representing a lower C1-4alkyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted benzyl group). The process provides an industrially excellent process for the preparation of a 4-substituted azetidinone derivative which permits the selective preparation of an intermediate for the synthesis of a carbapenem antibacterial agent having a desired 1-β′ configuration.

Highly stereocontrolled synthesis of the 1β-methylcarbapenem key intermediate by the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with a 4-acetoxy-2-azetidinone

The key synthetic intermediate (4) of 1β-methylcarbapenems (1~3) was efficiently synthesized by employing highly stereocontrolled Reformatsky reaction (C4-alkylation) of 3-(2-bromopropionyl)-2-oxazolidone derivatives (6) with (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidino ne (5) in the presence of zinc dust followed by removal of 2-oxazolidone moieties. The best diastereoselectivity (β:α = 95:5) could be realized by uses of sterically crowded achiral 2-oxazolidone derivatives such as 4,4-dimethyl-, 4,4,5,5-tetramethyl, and 4,4-dibutyl-5,5-pentamethylene-2-oxazolidone and higher reaction temperatures (refluxing tetrahydrofran). The remarkable diastereoselectivities observed for the Reformatsky reactions could be explained by means of the weakly chelating transition state models.

A highly stereoselective synthesis of a key intermediate of 1β-methylcarbapenems employing the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives

-