Benzene → HCID 86741780, compound

HRID 2309082Notes

Reaction equation

HRID 2309082 reaction equation
[CH3:1][O:2][C:3](=[O:35])[C:4]([N:8]1[C@H:11]([S:12]SC2SC3C=CC=CC=3N=2)[C@@H:10]([O:23][C:24](=[O:33])[CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:9]1=[O:34])=[C:5]([CH3:7])[CH3:6].[BH4-].[Na+].[C:38](Br)(=[O:40])[CH3:39].C1C=CC=CC=1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:35])[C:4]([N:8]1[C@H:11]([S:12][C:38](=[O:40])[CH3:39])[C@@H:10]([O:23][C:24](=[O:33])[CH2:25][O:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:9]1=[O:34])=[C:5]([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 241BenzeneHCID 10482Acetyl bromideHCID 4311764Sodium borohydrideHCID 56614980HCID 56614980, compound

Product 1

HCID 86741780HCID 86741780, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 687 mg (1.29 mmole) of 2-[(3S,4R)-4-(benzthiazol-2-yldithio)-3-phenoxyacetoxy-2-oxoazetidin-1-yl]-3-methylcrotonic acid methyl ester in 14 ml of dimethylformamide is added to a solution, cooled to -20°, of 76 mg (2 mmole) of sodium borohydride in 10 ml of dimethylformamide and the mixture is stirred at the same temperature for 10 minutes. 7 ml of freshly distilled acetyl bromide are added to the reaction mixture, which is further stirred at 0° for 40 minutes. After adding 400 ml of benzene, the reaction mixture is washed in succession with aqueous sodium bicarbonate solution, water and sodium chloride solution, dried over sodium sulphate and concentrated by evaporation in vacuo. After chromatography over silica gel with toluene/ethyl acetate (19:1) the residue yields the title compound in the form of an oil, which is further purified on silica gel plates with toluene/ethyl acetate (4:1). The title compound is obtained in oily form.

Workup

  1. stirringis further stirred at 0° for 40 minutes
  2. washthe reaction mixture is washed in succession with aqueous sodium bicarbonate solution, water and sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-f87edf64806b48a3833bfd648421e3cd
Source dataset
uspto-grants-1987_09
Patent number
US04692442

Reaction notes

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