Hydrogen Peroxide → HCID 24983448, compound

HRID 1925205Notes

Reaction equation

HRID 1925205 reaction equation
[C:1]([Si:5]([CH3:37])([CH3:36])[O:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:15](=[O:24])[C@@H:14]2[CH2:25][CH2:26][C:27]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[O:28])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].CO.OO.S(=O)(=O)(O)O>O>[C:1]([Si:5]([CH3:37])([CH3:36])[O:6][C:7]1[CH:8]=[CH:9][C:10]([C@H:13]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:15](=[O:24])[C@@H:14]2[CH2:25][CH2:26][C@@H:27]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[OH:28])=[CH:11][CH:12]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 1118Sulfuric AcidHCID 24983447HCID 24983447, compound

Product 1

HCID 24983448HCID 24983448, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.00 g (9.6 mmol) (3R,4S)-4-[4-(tert-butyl-dimethyl-silanyl-oxy)-phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxo-propyl]-azetidin-2-on was solved in 9.6 ml water-free dichloromethane, and then 1.92 ml (0.96 mmol) (R)-o-tolyl-CBS-oxazaborolidine 0.5 M-toluenic solution was added. The mixture was cooled to a temperature between 0 and −5° C., and at this temperature a dichloromethanic solution of 1.9 ml 1.0 M borane-dimethyl was added for 6 h. The reaction mixture had been stirred at this temperature until the spot of the starting keton disappeared according to the thin-layer chromatographic investigation. Then 10 ml methanol, 0.5 ml 5% hydrogen-peroxide solution, and 10 ml 2M sulphuric acid were added. Having been stirred the mixture for 0.5 h, the phases were separated. The organic phase was washed with 50 ml 2N sulphuric acid and then 50 ml 5% sulphite-solution. The solution was dried on anhydrous sodium-sulphate, filtered and evaporated.

Workup

  1. temperatureThe mixture was cooled to a temperature between 0 and −5° C.
  2. stirringHaving been stirred the mixture for 0.5 h
  3. customthe phases were separated
  4. washThe organic phase was washed with 50 ml 2N sulphuric acid
  5. dry with materialThe solution was dried on anhydrous sodium-sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-f84e6f93eb8c4b11a0ef90a308dd2b2c
Source dataset
uspto-grants-2012_05
Patent number
US08178665B2

Reaction notes

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