4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-[4-[2-(4-Bromo-benzyl)-4,5-dimethyl-furan-3-carbonyl]-2,6-diisopropyl-phenoxysulfonyl]-2-hydroxy-benzoic Acid
Reaction equation
[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[O:8][C:9]([CH3:28])=[C:10]([CH3:27])[C:11]=2[C:12]([C:14]2[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[C:17]([OH:23])=[C:16]([CH:24]([CH3:26])[CH3:25])[CH:15]=2)=[O:13])=[CH:4][CH:3]=1.Cl[S:32]([C:35]1[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[C:37]([OH:44])[CH:36]=1)(=[O:34])=[O:33]>>[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[O:8][C:9]([CH3:28])=[C:10]([CH3:27])[C:11]=2[C:12]([C:14]2[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[C:17]([O:23][S:32]([C:35]3[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[C:37]([OH:44])[CH:36]=3)(=[O:34])=[O:33])=[C:16]([CH:24]([CH3:25])[CH3:26])[CH:15]=2)=[O:13])=[CH:4][CH:3]=1Participants
3
Procedure
The title compound was prepared according to the procedure in Example 4 using [2-(4-bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-hydroxy-phenyl)-methanone (1.30 g, 2.77 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (1.00 g, 4.22 mmol). Purification on Dynamax C18 (90% CH3CN/H2O) gave 0.98 g (53%) of the title compound as an off white solid, mp 165-168° C. 1H NMR (DMSO-d6) δ 1.05 (d, 12H), 1.80 (s, 3H), 2.19 (s, 3H), 3.06 (septet, 2H), 3.81 (s, 2H), 6.92 (d, 2H), 7.39 (dd, 2H), 7.44 (s, 1H), 7.45 (s, 2H), 7.48 (d, 1H), 8.05 (d, 1H). IR (KBr) 3400, 2950, 1680, 1375 and 1190 cm−1. mass spectrum (−ESI) m/z 667 (M−H). Anal. Calcd. for C33H33BrO8S: C, 59.20; H, 4.97; N, 0.00. Found: C, 59.18; H, 5.21; N, 0.08.
Workup
- customThe title compound was prepared
- customPurification on Dynamax C18 (90% CH3CN/H2O)
Sources & evidence
- ORD record
- ord-43ed8698865340d080db8ad816541c10
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06451845B1
Reaction notes
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