4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-[4-(2-Benzyl-4,5-dimethyl-furan-3-carbonyl)-2,6-diethyl-phenoxysulfonyl]-2-hydroxy-benzoic Acid
Reaction equation
[CH2:1]([C:8]1[O:9][C:10]([CH3:27])=[C:11]([CH3:26])[C:12]=1[C:13]([C:15]1[CH:20]=[C:19]([CH2:21][CH3:22])[C:18]([OH:23])=[C:17]([CH2:24][CH3:25])[CH:16]=1)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[S:29]([C:32]1[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[C:34]([OH:41])[CH:33]=1)(=[O:31])=[O:30]>>[CH2:1]([C:8]1[O:9][C:10]([CH3:27])=[C:11]([CH3:26])[C:12]=1[C:13]([C:15]1[CH:16]=[C:17]([CH2:24][CH3:25])[C:18]([O:23][S:29]([C:32]2[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[C:34]([OH:41])[CH:33]=2)(=[O:31])=[O:30])=[C:19]([CH2:21][CH3:22])[CH:20]=1)=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
3
Procedure
The title compound was prepared according to the procedure in Example 4 using (2-benzyl-4,5-dimethyl-furan-3-yl)-(3,5-diethyl-4-hydroxy-phenyl)-methanone (0.5 g, 1.38 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.65 g, 2.74 mmol). Purification on 2% H3PO4/MeOH treated silica gel, eluting with 10% EtOAc/hexane gave 0.251 g (32%) of the title compound as an off white solid, mp 143-147° C. 1H NMR (DMSO-d6) δ 1.01 (t, 6H), 1.84 (s, 3H), 2.20 (s, 3H), 2.51 (q, 4H, with DMSO peak), 3.81 (s, 2H), 7.01 (d, 2H), 7.16-7.20 (m, 1H), 7.23-7.27 (m, 2H), 7.45 (s, 2H), 7.49-7.53 (m, 2H), 8.06 (d, 1H). mass spectrum (−ESI), m/z 561 (M−H). Anal. Calcd. for C31H30O8S: C, 66.18; H, 5.37; N, 0.00. Found: C, 65.80; H, 5.50; N, 0.22.
Workup
- customThe title compound was prepared
- customPurification on 2% H3PO4/MeOH
- additiontreated silica gel
- washeluting with 10% EtOAc/hexane
Sources & evidence
- ORD record
- ord-54843460c6f840f2b85a014dc9dc0f09
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06451845B1
Reaction notes
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