2-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-oxoacetic acid 2,2,2-trichloroethyl ester → (3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidine

HRID 2309087Notes

Reaction equation

HRID 2309087 reaction equation
ClC(Cl)(Cl)COC(=O)C([N:8]1[C@H:11]([S:12][C:13](=[O:15])[CH3:14])[C@@H:10]([O:16][CH3:17])[C:9]1=[O:18])=O>CO.C(OC)(=O)C.O>[C:13]([S:12][C@H:11]1[NH:8][C:9](=[O:18])[C@@H:10]1[O:16][CH3:17])(=[O:15])[CH3:14]

Participants

5

Reactant 1

HCID 867417832-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-oxoacetic acid 2,2,2-trichloroethyl ester

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6584Methyl AcetateSolvent

Procedure

A solution of 1.52 g of 2-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-oxoacetic acid 2,2,2-trichloroethyl ester (crude product) in 290 ml of methanol, 40 ml of methyl acetate and 5.9 ml of water is refluxed for 20 minutes under nitrogen. The solvent is evaporated off in vacuo. After chromatography over silica gel with toluene/ethyl acetate (3:1) the residue yields the title compound.

Workup

  1. customThe solvent is evaporated off in vacuo

Sources & evidence

ORD record
ord-d31a71601008434e88799e95dee93b62
Source dataset
uspto-grants-1987_09
Patent number
US04692442

Reaction notes

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