4-Acetylthio-2-azetidinone → 1-(Allyloxycarbonylhydroxymethyl)-4-acetylthioazetidin-2-one

HRID 1446969Notes

Reaction equation

HRID 1446969 reaction equation
[C:1]([S:4][CH:5]1[NH:8][C:7](=[O:9])[CH2:6]1)(=[O:3])[CH3:2].O.[C:11]([O:15][CH2:16][CH:17]=[CH2:18])(=[O:14])[CH:12]=[O:13]>C1C=CC=CC=1>[CH2:16]([O:15][C:11]([CH:12]([OH:13])[N:8]1[CH:5]([S:4][C:1](=[O:3])[CH3:2])[CH2:6][C:7]1=[O:9])=[O:14])[CH:17]=[CH2:18]

Participants

4

Reactant 2

HCID 131320584-Acetylthio-2-azetidinoneHCID 21908969Allyl glyoxylate monohydrate

Product 1

HCID 205520001-(Allyloxycarbonylhydroxymethyl)-4-acetylthioazetidin-2-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Acetylthioazetidin-2-one (Annalen, 1974, p. 553) (1.4 g) and allyl glyoxylate hydrate (1.5 g) are refluxed for 2 hours in benzene to afford a solution of 1-(allyloxycarbonylhydroxymethyl)-4-acetylthioazetidin-2-one which is cooled and used directly in the next step.

Sources & evidence

ORD record
ord-69d5231ee89e4b2b8e6d0abfde0af1c9
Source dataset
uspto-grants-1982_02
Patent number
US04314942

Reaction notes

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