HCID 14460291, compound → HCID 23035702, compound

HRID 2309072Notes

Reaction equation

HRID 2309072 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 0.33 ml of thioacetic acid in 4.5 ml of 1N sodium hydroxide solution is added dropwise at room temperature under a nitrogen atmosphere to a solution of 438 mg (3.06 mmoles) of 4-acetoxy-3-methylazetidin-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 1.13 ml of water and 0.27 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 silica gel with toluene/ethyl acetate (4:1 to 3:2) and yields first of all the pure trans-compound, then a mixture of the cis- and trans-isomers of the title compound and subsequently the pure cis-compound.

Workup

  1. customproduced
  2. additionracemic mixture of cis- and trans-isomer in a ratio of 3:1
  3. extractionThe reaction mixture is exhaustively extracted with methylene chloride
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated by evaporation in vacuo
  6. customThe residue is chromatographed over silica gel with toluene/ethyl acetate (4:1 to 3:2)
  7. customyields first of all the pure trans-compound

Sources & evidence

ORD record
ord-8279cc7a82ab44f69858928e8cb5a7e2
Source dataset
uspto-grants-1987_09
Patent number
US04692442

Reaction notes

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