Iodoethane → 4-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(5-ethoxymethyl-4'-methanesulfonyl-biphenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:47])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([C:30]3[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=3)[CH:25]=[C:26]([CH2:28][OH:29])[CH:27]=2)[C:10]=1[CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH3:2].[H-].[Na+].I[CH2:51][CH3:52]>>[CH2:1]([O:3][C:4](=[O:47])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([C:30]3[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=3)[CH:25]=[C:26]([CH2:28][O:29][CH2:51][CH3:52])[CH:27]=2)[C:10]=1[CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH3:2]Participants
4
Reactant 3
Product 1
Procedure
A similar procedure as described in Example 24, step 1 was used, starting from 4-{2-(2-ethoxycarbonyl-ethyl)-3-[6-(5-hydroxymethyl-4′-methanesulfonyl-biphenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid ethyl ester (250 mg, 0.37 mmol), sodium hydride (29.9 mg, 0.75 mmol), and iodoethane (116.7 mg, 0.75 mmol) to obtain 4-{2-(2-ethoxycarbonyl-ethyl)-3-[6-(5-ethoxymethyl-4′-methanesulfonyl-biphenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid ethyl ester (110 mg, 42%) as a light brown oil: ES(+)-HRMS m/e calcd for C39H52O9S (M+Na)+ 719.3224, found 719.3227.
Sources & evidence
- ORD record
- ord-d3b650199c554a389d11ea6f5a3d2580
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088936B2
Reaction notes
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