Sodium Chloride → HCID 86753533, compound

HRID 342289Notes

Reaction equation

HRID 342289 reaction equation
[N+:1]([C:4]1[CH:30]=[CH:29][C:7]([CH2:8][O:9][C:10]([O:12][C@@H:13]([C@@H:15]2[C@@H:18]([C:19]#[C:20][S:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:17][C:16]2=[O:28])[CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].FC(F)(F)C(O)=[O:34].C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C(Cl)Cl.C(OCC)(=O)C.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([O:12][C@@H:13]([C@@H:15]2[C@@H:18]([CH2:19][C:20]([S:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:34])[NH:17][C:16]2=[O:28])[CH3:14])=[O:11])=[CH:29][CH:30]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 13471478HCID 13471478, compound

Product 1

HCID 86753533HCID 86753533, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 448 mg of (3S, 4S)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-4-[(phenylthio)ethynyl]-2-azetidinone in 5 ml of anhydrous methylene chloride was added, under an atmosphere of nitrogen gas, 0.4 ml of trifluoroacetic acid, with stirring and ice-cooling. Stirring was continued 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 1.0 g of sodium bicarbonate, 10 ml of water and 20 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 dried over anhydrous magnesium sulphate. The solvent was distilled off under reduced pressure and the residue was subjected to column chromatography through silica gel, eluted with a 1:1 by volume mixture of cyclohexane and ethyl acetate, to afford 95.0 mg (yield 63.0%) of the title thioester compound, as a viscous oil.

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 dried over anhydrous magnesium sulphate
  6. distillationThe solvent was distilled off under reduced pressure
  7. washeluted with a 1:1 by volume mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-c590f632128245078f67bde4c7ececdc
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

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