Sodium Chloride → HCID 13219837, compound

HRID 342299Notes

Reaction equation

HRID 342299 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@H:14]([C:15]#[C:16][S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:13][C:12]1=[O:24])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].FC(F)(F)C(O)=[O:28].C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C(Cl)Cl.C(OCC)(=O)C.O>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([S:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:28])[NH:13][C:12]1=[O:24])[CH3:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 70450331HCID 70450331, compound

Product 1

HCID 13219837HCID 13219837, compoundYield 89.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.28 g of (3S, 4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-4-[(phenylthio)ethynyl]-2-azetidinone in 75.0 ml of anhydrous methylene chloride were added, under an atmosphere of nitrogen gas, 3.5 ml of trifluoroacetic acid, with stirring and ice-cooling. The mixture was then stirred for 30 minutes under ice-cooling and for a further 1.5 hours at room temperature. The reaction mixture was then poured into a mixture of 1.14 g of sodium bicarbonate, 75 ml of water and 300 ml of ethyl acetate. The mixture was saturated with sodium chloride and the organic layer was separated. The aqueous layer was extracted twice with ethyl acetate. The organic layer and the ethyl acetate extracts were combined, and the combined solution was washed successively with an aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulphate. The solvent was distilled off under reduced pressure and the residue was subjected to column chromatography through silica gel, eluted with a 3:1 by volume mixture of cyclohexane and ethyl acetate, to give 3.09 g (yield 89.9%) of the title thioester compound, melting at 94°-95° C.

Workup

  1. temperatureice-cooling
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. washthe combined solution was washed successively with an aqueous solution of sodium bicarbonate
  5. dry with materiala saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulphate
  6. distillationThe solvent was distilled off under reduced pressure
  7. washeluted with a 3:1 by volume mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-ba1633fea39c4c018f18f75f5988fe89
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

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