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

HRID 1710236Notes

Reaction equation

HRID 1710236 reaction equation
COC(=O)C([N:6]1[C@H:9]([S:10][C:11](=[O:13])[CH3:12])[C@@H:8]([O:14][CH3:15])[C:7]1=[O:16])=O>CO.C(Cl)Cl>[C:11]([S:10][C@H:9]1[NH:6][C:7](=[O:16])[C@@H:8]1[O:14][CH3:15])(=[O:13])[CH3:12]

Participants

4

Reactant 1

HCID 867417792-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-oxoacetic acid methyl ester

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 71.20 mg of 2[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl-2-oxoacetic acid methyl ester (crude product) in 10 ml of 1% aqueous methanol is stirred overnight at room temperature. The reaction mixture is diluted with methylene chloride, washed with water, dried over sodium sulphate and concentrated by evaporation in vacuo. The residue is chromatographed over silica gel with toluene/ethyl acetate (9:1) and yields the title compound.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated by evaporation in vacuo
  4. customThe residue is chromatographed over silica gel with toluene/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-0a48b089b0b9408e8e2ec64daeab463c
Source dataset
uspto-grants-1990_08
Patent number
US04952690

Reaction notes

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