Sodium Chloride → HCID 57172225, compound

HRID 622440Notes

Reaction equation

HRID 622440 reaction equation
B(F)(F)F.CCOCC.[Si]([O:17][C@@H:18]([C@@H:20]1[C@@H:23]([CH:24]([C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[S:27])[CH3:25])[NH:22][C:21]1=[O:34])[CH3:19])(C(C)(C)C)(C)C.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C(#N)C>[OH:17][C@@H:18]([C@@H:20]1[C@@H:23]([CH:24]([C:26]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[S:27])[CH3:25])[NH:22][C:21]1=[O:34])[CH3:19]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 57233136HCID 57233136, compound

Product 1

HCID 57172225HCID 57172225, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.3 ml of boron trifluoride etherate were added to a solution of 1.37 g of (3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1RS)-1-(phenylthiocarbonyl)ethyl]-2-azetidinone in 33 ml of acetonitrile, cooled in ice-water, and the mixture was stirred for 15 minutes at 0° to 5° C. 2.94 g of sodium bicarbonate were added to the reaction mixture, then a saturated aqueous sodium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was stripped off, giving 0.95 g of (3S,4S)-3-[(1R)-1-hydroxyethyl]-4-[(1RS)-1-(phenylthiocarbonyl)ethyl]-2-azetidinone, which was used in the following reaction.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-7c8041042db34d96a74760b258040475
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

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