Potassium Bromide → 4-[3-Bromo-5-(8-phenyl-octylcarbamoyl)-3'-trifluoromethyl-biphenyl-2-yloxysulfonyl]-2-hydroxy-benzoic acid
Reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([C:18]2[CH:19]=[C:20]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[C:21]([OH:25])=[C:22]([Br:24])[CH:23]=2)=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[S:37]([C:40]1[CH:48]=[CH:47][C:43]([C:44]([OH:46])=[O:45])=[C:42]([OH:49])[CH:41]=1)(=[O:39])=[O:38].[K+].[Br-]>>[Br:24][C:22]1[C:21]([O:25][S:37]([C:40]2[CH:48]=[CH:47][C:43]([C:44]([OH:46])=[O:45])=[C:42]([OH:49])[CH:41]=2)(=[O:39])=[O:38])=[C:20]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:33])[F:34])[CH:27]=2)[CH:19]=[C:18]([C:16](=[O:17])[NH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:23]=1Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared as an orange foam (0.455 g, 76%) from 5-bromo-6-hydroxy-3′-trifluoromethyl-biphenyl-3-carboxylic acid (8-phenyl-octyl)-amide and 4-chlorosulfonyl-2-hydroxy-benzoic acid using a procedure similar to step 3 of Example 179. 1H NMR (DMSO-d6) 12.60 (bs, 1H); 11.60 (bs, 1H); 8.68 (t, 1H); 8.21 (d, 1H); 7. 84 (d, 1H); 7.71-7.62 (m, 2H); 7.56-7.44 (m, 3H); 7.26-7.10 (m, 5H); 6.96 (dd, 1H); 6.82 (d, 1H); 3.21 (dd, 2H); 2.62 (t, 4H); 2.53 (t, 2H); 1.52 (m, 4H); 1.25 (m, 8H); IR (KBr) 3370, 2950, 2825, 1690, 1640, 1605, 1560, 1540, 1390, 1325, 1195, 1170, 1125 cm−1; mass spectrum [(−)ESI], m/z 660/662 (M−H)−; Anal. Calcd. for C35H33BrF3NO7S: C, 56.16; H, 4.44; N, 1.87, Found: C, 55.65; H, 4.27; N, 1.90.
Sources & evidence
- ORD record
- ord-97f527f85277421ba4eb646f92d6812f
- Source dataset
- uspto-grants-2004_07
- Patent number
- US06765021B2
Reaction notes
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