Sodium methanesulfinate → HCID 54422945, compound

HRID 653240Notes

Reaction equation

HRID 653240 reaction equation
C([O:4][C@@H:5]1[NH:8][C:7](=O)[C@H:6]1[NH:10][C:11](=[O:20])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)C.[CH3:21][S:22]([O-:24])=[O:23].[Na+]>CO>[CH3:21][S:22]([C@@H:7]1[NH:8][C:5](=[O:4])[C@H:6]1[NH:10][C:11](=[O:20])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 11821934HCID 11821934, compound

Product 1

HCID 54422945HCID 54422945, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.494 g of (3S,4S)-4-acetoxy-3-phenoxyacetamido-2-oxoazetidine in 14 ml of 50% methanol is added 0.51 g of sodium methylsulfinate and the mixture is stirred at room temperature for 18 hours. The methanol is distilled off under reduced pressure to give 222 mg of (3R,4S)-4-methylsulfonyl-3-phenoxyacetamido-2-oxoazetidine.

Workup

  1. distillationThe methanol is distilled off under reduced pressure

Sources & evidence

ORD record
ord-cc207d5233bd4a0395e77cff075f3244
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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