4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-{4-[2-(4-Bromo-benzyl)-4,5-dimethyl-thiophene-3-carbonyl]-2-cyclopentyl-phenoxysulfonyl}-2-hydroxy-benzoic Acid

HRID 1280929Notes

Reaction equation

HRID 1280929 reaction equation
[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[S:8][C:9]([CH3:27])=[C:10]([CH3:26])[C:11]=2[C:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:15]=2)=[O:13])=[CH:4][CH:3]=1.Cl[S:31]([C:34]1[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[C:36]([OH:43])[CH:35]=1)(=[O:33])=[O:32]>>[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[S:8][C:9]([CH3:27])=[C:10]([CH3:26])[C:11]=2[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][S:31]([C:34]3[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[C:36]([OH:43])[CH:35]=3)(=[O:33])=[O:32])=[C:16]([CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:15]=2)=[O:13])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acidHCID 15895037[2-(4-Bromobenzyl)-4,5-dimethyl-thiophen-3-yl]-(3-cyclopentyl4-hydroxy-phenyl)-methanone

Product 1

HCID 103052134-{4-[2-(4-Bromo-benzyl)-4,5-dimethyl-thiophene-3-carbonyl]-2-cyclopentyl-phenoxysulfonyl}-2-hydroxy-benzoic AcidYield 38.3%

Procedure

The title compound was prepared according to the procedure in Example 4 using [2-(4-bromobenzyl)-4,5-dimethyl-thiophen-3-yl]-(3-cyclopentyl-4-hydroxy-phenyl)-methanone (1.01 g, 2.14 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (1.01 g, 4.29 mmol). Purification on 2% H3PO4/MeOH treated silica gel, eluting with a 15 & 25% EtOAc/hexane step gradient followed by crystallization from ether/pet ether gave 0.549 g (38%) of the title compound as a tan solid, mp 165-170° C. 1H NMR (DMSO-d6) δ 1.22-1.32 (m, 2H), 1.46-1.58 (m, 2H), 1.61-1.76 (m, 4H), 1.78 (s, 3H), 2.26 (s, 3H), 2.97 (quintet, 1H), 3.84 (s, 2H), 6.94 (d, 2H), 7.23 (d, 1H), 7.34-7.40 (m, 4H), 7.50 (dd, 1H), 7.53 (d, 1H), 8.00 (d, 1H). IR (KBr) 3400, 2950, 1680, 1480, 1390 and 1190 cm−1. mass spectrum (−ESI) m/z 667 (M−H). Anal. Calcd. for C32H29BrO7S2: C, 57.40; H, 4.37; N, 0.00. Found: C, 57.47; H, 4.24; N, 0.08.

Workup

  1. customThe title compound was prepared
  2. customPurification on 2% H3PO4/MeOH
  3. additiontreated silica gel
  4. washeluting with a 15 & 25% EtOAc/hexane step gradient
  5. customfollowed by crystallization from ether/pet ether

Sources & evidence

ORD record
ord-c9bd00d9504d4563a7c2d947c1a0d140
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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