Acetic Anhydride → 1-Acetyl-4-(methylthio)azetidin-2-one

HRID 484035Notes

Reaction equation

HRID 484035 reaction equation
[CH3:1][S:2][CH:3]1[NH:6][C:5](=[O:7])[CH2:4]1.[C:8](OC(=O)C)(=[O:10])[CH3:9]>N1C=CC=CC=1>[C:8]([N:6]1[CH:3]([S:2][CH3:1])[CH2:4][C:5]1=[O:7])(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 126772484-(Methylsulfanyl)azetidin-2-one

Product 1

HCID 145437851-Acetyl-4-(methylthio)azetidin-2-oneYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 300 mg (2.6 mM) 4-methylthioazetidin-2-one, 10 ml acetic anhydride and 10 ml pyridine was stirred at 100° in a sealed tube 24 hours. After concentrating in vacuo, the residue was chromatographed on silica gel in hexane/ethyl acetate to yield 324 mg (78%) of 1-acetyl-4-methylthioazetidine-2-one.

Workup

  1. concentrationAfter concentrating in vacuo
  2. customthe residue was chromatographed on silica gel in hexane/ethyl acetate

Sources & evidence

ORD record
ord-3b89746b15c2414ab793d37bcf05c07f
Source dataset
uspto-grants-1993_07
Patent number
US05229381

Reaction notes

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