(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 1710241Notes

Reaction equation

HRID 1710241 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-1a374dd88f2448a387db1cd1df82551d
Source dataset
uspto-grants-1990_08
Patent number
US04952690

Reaction notes

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