1,4-Dioxane → (3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidine

HRID 1710245Notes

Reaction equation

HRID 1710245 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[Na+].C(O[C@@H:10]1[NH:13][C:12](=[O:14])[C@H:11]1[O:15][CH3:16])(=O)C.O1CCOCC1>P([O-])([O-])([O-])=O>[C:1]([S:3][C@H:10]1[NH:13][C:12](=[O:14])[C@@H:11]1[O:15][CH3:16])(=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 23700354HCID 23700354, compoundHCID 56607243(3S,4S)-4-acetoxy-3-methoxy-2-oxoazetidine

Product 1

HCID 56630779(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidine

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

1.5 equivalents of an aqueous sodium thioacetate solution are added to a solution of 40 mg of (3S,4S)-4-acetoxy-3-methoxy-2-oxoazetidine (for manufacture see below) in 1.5 ml of phosphate buffer of a pH of 7 and 0.1 ml of dioxan, and the mixture is stirred for 30 minutes at room temperature. The reaction mixture is extracted with methylene chloride and the separated organic solution is then dried over sodium sulphate. The solvent is evaporated off in vacuo and the residue is purified by chromatography over silica gel with toluene/ethyl acetate (3:1). The IR spectrum of the resulting title compound (in methylene chloride) is identical to that of the product obtained according to a).

Workup

  1. extractionThe reaction mixture is extracted with methylene chloride
  2. dry with materialthe separated organic solution is then dried over sodium sulphate
  3. customThe solvent is evaporated off in vacuo
  4. customthe residue is purified by chromatography over silica gel with toluene/ethyl acetate (3:1)
  5. customobtained

Sources & evidence

ORD record
ord-17814ec178ed4e76944bf29db7b8a9ed
Source dataset
uspto-grants-1990_08
Patent number
US04952690

Reaction notes

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