4-(Chlorosulfonyl)-2-hydroxybenzoic acid → HCID 10281572, compound

HRID 1280916Notes

Reaction equation

HRID 1280916 reaction equation
[CH2:1]([C:8]1[O:9][C:10]([CH3:28])=[C:11]([CH3:27])[C:12]=1[C:13]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:16]=1)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[S:30]([C:33]1[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[C:35]([OH:42])[CH:34]=1)(=[O:32])=[O:31]>>[CH2:1]([C:8]1[O:9][C:10]([CH3:28])=[C:11]([CH3:27])[C:12]=1[C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][S:30]([C:33]2[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[C:35]([OH:42])[CH:34]=2)(=[O:32])=[O:31])=[C:17]([CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:16]=1)=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acidHCID 23445653HCID 23445653, compound

Product 1

HCID 10281572HCID 10281572, compoundYield 55%

Procedure

The title compound was prepared according to the procedure in Example 4 using (2-benzyl-4,5-dimethyl-furan-3-yl)-(3-cyclopentyl-4-hydroxy-phenyl)-methanone (0.509 g, 1.36 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.645 g, 2.72 mmol). Purification on 2% H3PO4/MeOH treated silica gel, eluting with 20% EtOAc/hexane gave 0.430 g (55%) of the title compound a pale yellow solid, mp 80-85° C. 1H NMR (DMSO-d6) δ 1.23-1.34 (m, 2H), 1.45-1.59 (m, 2H), 1.61-1.74 (m, 4H), 1.76 (s, 3H), 2.16 (s, 3H), 2.95 (quintet, 1H), 3.78 (s, 2H), 6.98 (d, 2H), 7.13-7.25 (m, 4H), 7.36-7.38 (m, 2H), 7.44-7.57 (m, 2H), 7.97 (d, 1H). IR (KBr) 3400, 2950, 1690, 1580, 1480 and 1190 cm−1. mass spectrum (−ESI) m/z 573 (M−H). Anal. Calcd. for C32H30O8S.0.2H2O: C, 66.88; H, 5.26; N, 0.00. Found: C., 66.53; H, 5.40; N, 0.07.

Workup

  1. customThe title compound was prepared
  2. customPurification on 2% H3PO4/MeOH
  3. additiontreated silica gel
  4. washeluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-ee2af269661e4a6c9ac3c9804f05f803
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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