p-Toluenesulfonic acid → HCID 22844619, compound
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH:13]([OH:16])[CH:14]=[CH2:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1(C)[CH:26]=CC(S(O)(=O)=O)=C[CH:22]=1.C(OCC)(=O)C>COC(OC)(C)C>[CH2:1]([O:8][C:9]([N:11]1[C@@H:12]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH:13]([CH:14]=[CH2:15])[O:16][C:21]1([CH3:26])[CH3:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
124 mg of (3RS,4S)-4-(benzyloxycarbonyl)amino-6-methylhepten-3-ol was dissolved in 0.33 ml of 2,2-dimethoxypropane, and 4 mg of dry p-toluenesulfonic acid was added thereto. The mixture was stirred at room temperature overnight. Then, 20 ml of ethyl acetate was added to the reaction solution, and the mixture was washed with a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1) to obtain 101 mg of (4S,5RS)-3-benzyloxycarbonyl-2,2-dimethyl-5-ethenyl-4-isobutyloxazolidine as colorless oily substance.
Workup
- washthe mixture was washed with a saturated sodium hydrogencarbonate aqueous solution
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1)
Sources & evidence
- ORD record
- ord-47605c6b04664539b0c7c99252037ba6
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05481036
Reaction notes
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