HCID 23035687, compound → HCID 23035765, compound

HRID 2309075Notes

Reaction equation

HRID 2309075 reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].C(O[CH:9]1[NH:12][C:11](=[O:13])[CH:10]1[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=O)C>[OH-].[Na+].O1CCOCC1>[C:1]([S:3][CH:9]1[NH:12][C:11](=[O:13])[CH:10]1[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:4])[CH3:2]

Participants

5

Reactant 2

HCID 23035687HCID 23035687, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 23035765HCID 23035765, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.76 g (10 mmole) of thioacetic acid in 10 ml of 1N sodium hydroxide solution is added dropwise to a solution of 2.19 g (10 mmole) of 4-acetoxy-3-benzylazetidin-2-one (racemic mixture of cis- and trans-isomer in the ratio of 9:13) in 10 ml of dioxan at room temperature under a nitrogen atmosphere, 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 (9:1) and yields a cis-trans mixture of the title compound in the ratio of 2:10. By recrystallisation from methylene chloride/hexane at -10° the pure trans-compound having a melting point of 42°-43° is obtained.

Workup

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

Sources & evidence

ORD record
ord-70b0aa12ce324a3bab6cdf14265c0cd5
Source dataset
uspto-grants-1987_09
Patent number
US04692442

Reaction notes

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