Hydrogen Peroxide → HCID 13477591, compound
Reaction equation
OO.[CH2:3]([O:10][C:11]([NH:13][CH:14]([CH2:28][F:29])[CH2:15][C@H:16]([Se]C1C=CC=CC=1)[C:17]([O:19][CH3:20])=[O:18])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CC(C)=O>[CH2:3]([O:10][C:11]([NH:13][C@H:14]([CH2:28][F:29])/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
4.2 ml of 30% hydrogen peroxide solution was added to a stirred solution of 1.4 g of 26A in 25 ml of acetone, at 0° C. The resulting solution was stirred at 0° C. for one hour, warmed to room temperature and the solvent was evaporated. The residue was diluted with 50 ml of cold water and 20 ml of 1N sodium bicarbonate solution and the resulting mixture was extracted with ethyl acetate. The extract was washed successively with water, 1N sodium bicarbonate solution and water, dried (MgSO4) and the solvent was evaporated. The residue was chromatographed on silica gel, first eluting with n-hexane, then with 25% ethyl acetate/n-hexane, to give, on work-up, methyl (S)-(E)-4-(benzyloxycarbonylamino)-5-fluoro-2-pentenoate (26B), as a pale yellow viscous oil.
Workup
- temperaturewarmed to room temperature
- customthe solvent was evaporated
- additionThe residue was diluted with 50 ml of cold water and 20 ml of 1N sodium bicarbonate solution
- extractionthe resulting mixture was extracted with ethyl acetate
- washThe extract was washed successively with water, 1N sodium bicarbonate solution and water
- dry with materialdried (MgSO4)
- customthe solvent was evaporated
- customThe residue was chromatographed on silica gel
- washfirst eluting with n-hexane
Sources & evidence
- ORD record
- ord-c994d266b97e459ba64fe43b5800b348
- Source dataset
- uspto-grants-1985_07
- Patent number
- US04528028
Reaction notes
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