Benzene → 3-(2-Ethoxycarbonyl-vinyl)-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH:14](C=O)[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:28]([CH:33]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:30][CH2:31][CH3:32])=[O:29].[CH:53]1C=CC=CC=1>>[C:1]([O:5][C:6]([CH:8]1[CH:14]([CH:53]=[CH:33][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=[O:7])([CH3:3])([CH3:2])[CH3:4]Participants
4
Reactant 3
Product 1
Procedure
To a solution of 3-Formyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester (310 mg, 0.78 mmoL) in 8.1 mL benzene was added (Carboethoxymethylene) triphenylphosphorane (408 mg, 1.17 mmoL) at ambient temperature. An additional 310 mg was added after 24 hours, after which the reaction was allowed to proceed for 72 hours. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph (silica: 18% to 25% ethyl acetate in hexanes) to yield 3-(2-Ethoxycarbonyl-vinyl)-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester; MS: (M+H)+ =468, (M+NHY4)- =485.
Workup
- additionAn additional 310 mg was added after 24 hours
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by column chromatograph (silica: 18% to 25% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-9ea43672d0ad4762aba5d2d69865f4e8
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06107291
Reaction notes
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