Dichloromethane → (3S)-3-carbobenzoxyamino-5-methyl-1,2-epoxyhexane
Reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[C:12]([NH:22][C@@H:23]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH:24]=[CH2:25])([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].ClCCl>C(Cl)(Cl)Cl>[C:12]([NH:22][C@@H:23]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH:24]1[O:6][CH2:25]1)([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13]Participants
Procedure
To a solution of 600 mg of 3-chloroperoxybenzoic acid in 5 ml of dry chloroform was added a solution of 850 mg of (3S)-3-carbobenzoxyamino-5-methyl-1-hexene in 5 ml of dry chloroform under ice-cooling, and the mixture was stirred for 16 hours. Dichloromethane was added to the reaction mixture, and the mixture was successively washed with an aqueous sodium thiosulfate solution, a 5% aqueous sodium bicarbonate solution and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: benzene/hexane=1/1 by volume) to obtain 401 mg of (3S)-3-carbobenzoxyamino-5-methyl-1,2-epoxyhexane as a colorless oil.
Workup
- temperaturecooling
- washthe mixture was successively washed with an aqueous sodium thiosulfate solution
- dry with materiala 5% aqueous sodium bicarbonate solution and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate
- customevaporated under reduced pressure
- customThe residue was purified by silica gel flash column chromatography (eluent: benzene/hexane=1/1 by volume)
Sources & evidence
- ORD record
- ord-407dd630696c4eb7bf7430abd8eb799d
- Source dataset
- uspto-grants-1989_06
- Patent number
- US04841067
Reaction notes
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