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

HRID 2309083Notes

Reaction equation

HRID 2309083 reaction equation
COC(=O)C([N:6]1[C@H:9]([S:10][C:11](=[O:13])[CH3:12])[C@@H:8]([O:14][C:15](=[O:24])[CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]1=[O:25])=O>CO.C(Cl)Cl>[C:11]([S:10][C@H:9]1[NH:6][C:7](=[O:25])[C@@H:8]1[O:14][C:15](=[O:24])[CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 1

HCID 56633453(3S,4R)-2-(4-acetylthio-3-phenoxyacetoxy-2-oxoazetidin-1-yl)-2-oxoacetic acid methyl ester

Product 1

HCID 56626630(3S,4R)-4-acetylthio-3-phenoxyacetoxy-2-oxoazetidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 129 mg (0.34 mmole) of (3S,4R)-2-(4-acetylthio-3-phenoxyacetoxy-2-oxoazetidin-1-yl)-2-oxoacetic acid methyl ester (crude product) in 10 ml of 1% aqueous methanol is stirred for 4 hours at room temperature. The reaction mixture is diluted with 50 ml of methylene chloride, washed in succession with water and saturated sodium chloride solution, 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 in succession with water and saturated sodium chloride solution
  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-ef9268db21754492b6ec97d1a3847ce5
Source dataset
uspto-grants-1987_09
Patent number
US04692442

Reaction notes

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