HCID 14460291, compound → HCID 23035702, compound

HRID 2309074Notes

Reaction equation

HRID 2309074 reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].C(O[CH:9]1[NH:12][C:11](=[O:13])[CH:10]1[CH3:14])(=O)C>[OH-].[Na+].O.CC(C)=O>[C:1]([S:3][CH:9]1[NH:12][C:11](=[O:13])[CH:10]1[CH3:14])(=[O:4])[CH3:2]

Participants

6

Reactant 2

HCID 14460291HCID 14460291, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 23035702HCID 23035702, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1.5 ml of thioacetic acid in 20.5 ml of 1N sodium hydroxide solution is added dropwise at room temperature, under nitrogen, to a solution of 2 g of 4-acetoxy-3-methyl-azetidin-2-one (produced according to K. Clauss et. al., Lieb. Ann. Chem., 1974, 539; racemic mixture of cis- and trans-isomer in a ratio of 3:1, Mp. 53°-65°) in 5.16 ml of water and 1.25 ml of acetone, and the mixture is stirred at the same temperature for 3 hours. The reaction mixture is exhaustively extracted with methylene chloride. The combined organic phases are dried over sodium sulphate and concentrated by evaporation in vacuo. The residue is chromatographed over 150 g of silica gel with toluene/ethyl acetate (9:1) and yields the almost pure trans-isomer of the title compound with the following physico-chemical properties:

Workup

  1. customproduced
  2. extractionThe reaction mixture is exhaustively extracted with methylene chloride
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated by evaporation in vacuo
  5. customThe residue is chromatographed over 150 g of silica gel with toluene/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-46ec3218193b400095e85f65f88cdf94
Source dataset
uspto-grants-1987_09
Patent number
US04692442

Reaction notes

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