Sodium Phosphate, Dibasic → Methyl (2R,3R)-3-azido-4-oxoazetidine-2-carboxylate

HRID 1974185Notes

Reaction equation

HRID 1974185 reaction equation
[N:1]([C@H:4]1[C:7](=[O:8])[N:6](CC2C=CC(OC)=CC=2OC)[C@H:5]1[C:20]([O:22][CH3:23])=[O:21])=[N+:2]=[N-:3].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].P([O-])([O-])(O)=O.[Na+].[Na+]>>[N:1]([C@H:4]1[C:7](=[O:8])[NH:6][C@H:5]1[C:20]([O:22][CH3:23])=[O:21])=[N+:2]=[N-:3]

Participants

4

Reactant 3

HCID 24203Sodium Phosphate, DibasicHCID 24412Potassium PersulfateHCID 86734328Methyl cis-1-(2,4-dimethoxybenzyl)-3-azido-4-oxoazetidine-2-carboxylate

Product 1

HCID 13566680Methyl (2R,3R)-3-azido-4-oxoazetidine-2-carboxylate

Procedure

A degassed solution of 3.8 g (0.012 mole) of methyl cis-3-azido-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate was treated with potassium persulfate and sodium monohydrogen phosphate as described in Preparation 2 to give methyl cis-3-azido-4-oxoazetidine-2-carboxylate which was purified by chromatography on silica gel with benzene-ethyl acetate as eluant.

Workup

  1. customas described in Preparation 2

Sources & evidence

ORD record
ord-28d3675aa8e541d893d90e9ddebc09cd
Source dataset
uspto-grants-1976_12
Patent number
US04000154

Reaction notes

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