Reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:29])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([O:27][CH3:28])[CH:21]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Br:30][CH2:31][CH2:32]Br.[OH-].[K+].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>>[Br:30][CH2:31][CH2:32][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][C:18]([NH:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([CH:8]3[CH2:9][CH2:10][CH:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:6][CH2:7]3)[CH:12]=2)=[O:29])=[CH:21][C:22]=1[O:27][CH3:28]Participants
5
Reactant 4
Product 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-4-hydroxy-3-methoxyphenylacetamide (the compound of Example 20) (1.5 g), 1,2-dibromethane (15 ml), 40% aqueous potassium hydroxide solution (5 ml) and 40% aqueous tetrabutylammonium hydroxide solution (0.5 ml) is stirred at 50° C. for 18 hours. The reaction solution is washed with water, and the organic layer is dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (1.6 g).
Workup
- washThe reaction solution is washed with water
- dry with materialthe organic layer is dried over sodium sulfate
- customthe solvent is evaporated under reduced pressure
- customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-c9a05f2f40394d91bbdcb528d65562fd
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07084176B2
Linked notes
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