N-benzenesulfonyl-4-ethinylbenzoic acid amide → 3-{3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-[2-(4-benzenesulfonamidocarbonylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester
Reaction equation
[C:1]1([S:7]([NH:10][C:11](=[O:20])[C:12]2[CH:17]=[CH:16][C:15]([C:18]#[CH:19])=[CH:14][CH:13]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][O:22][C:23](=[O:48])[CH2:24][CH2:25][C:26]1[C:31]([O:32][CH2:33][CH2:34][CH2:35][CH2:36]/[CH:37]=[CH:38]/[C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)=[CH:30][CH:29]=[C:28](I)[N:27]=1>>[CH3:21][O:22][C:23](=[O:48])[CH2:24][CH2:25][C:26]1[C:31]([O:32][CH2:33][CH2:34][CH2:35][CH2:36]/[CH:37]=[CH:38]/[C:39]2[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=2)=[CH:30][CH:29]=[C:28]([C:19]#[C:18][C:15]2[CH:14]=[CH:13][C:12]([C:11]([NH:10][S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:8])=[O:9])=[O:20])=[CH:17][CH:16]=2)[N:27]=1Participants
3
Reactant 2
Product 1
Procedure
Under the conditions of example 5 A, 1.31 g of the crude N-benzenesulfonyl-4-ethinylbenzoic acid amide is reacted with 1.9 g of 3-{6-iodo-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester, worked up, and the crude product is chromatographed on silica gel with dichloromethane/0-5% methanol. 750 mg of 3-{3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-[2-(4-benzenesulfonamidocarbonylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester is obtained as oil.
Workup
- customthe crude product is chromatographed on silica gel with dichloromethane/0-5% methanol
Sources & evidence
- ORD record
- ord-beb9ae21e7e7406597b47c3add4334d1
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05624943
Reaction notes
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