4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-{4-[2-(3-Bromo-benzyl)-4,5-dimethyl-furan-3-carbonyl]-2,6-diisopropyl-phenoxysulfonyl}-2-hydroxy-benzoic Acid
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][C:6]1[O:7][C:8]([CH3:27])=[C:9]([CH3:26])[C:10]=1[C:11]([C:13]1[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]([OH:22])=[C:15]([CH:23]([CH3:25])[CH3:24])[CH:14]=1)=[O:12].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:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][C:6]1[O:7][C:8]([CH3:27])=[C:9]([CH3:26])[C:10]=1[C:11]([C:13]1[CH:14]=[C:15]([CH:23]([CH3:24])[CH3:25])[C:16]([O:22][S:32]([C:35]2[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[C:37]([OH:44])[CH:36]=2)(=[O:34])=[O:33])=[C:17]([CH:19]([CH3:21])[CH3:20])[CH:18]=1)=[O:12]Participants
Reactant 2
Product 1
Procedure
The title compound was prepared according to the procedure in Example 4 using [2-(3-bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-hydroxy-phenyl)-methanone (0.300 g, 0.639 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.197 g, 0.831 mmol). Purification on Dynamax C18 (95% CH3CN/H2O) gave 0.23 g (54%) of the title compound as an off white solid, mp 148° C. 1H NMR (DMSO-d6) δ1.06 (d, 12H), 1.80 (s, 3H), 2.21 (s, 3H), 3.08 (septet, 2H), 3.87 (s, 2H), 7.04 (d, 1H), 7.21 (t, 1H), 7.25 (s, 1H), 7.38 (d, 1H), 7.44 (s, 1H), 7.48 (dd, 1H), 7.51 (s, 2H), 8.06 (d, 1H). IR (KBr) 3400, 2950, 1680, 1650 and 1180 cm−1. mass spectrum (−ESI) m/z 667 (M−H). Anal. Calcd. for C33H33BrO8S: C, 59.19; H, 4.97; N, 0.00. Found: C, 58.86; H, 4.93; N, 0.07.
Workup
- customThe title compound was prepared
- customPurification on Dynamax C18 (95% CH3CN/H2O)
Sources & evidence
- ORD record
- ord-8329daf11818433791e666f9f071043c
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06248764B1
Reaction notes
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