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

HRID 1280907Notes

Reaction equation

HRID 1280907 reaction equation
[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[O: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[O: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 23445642[2-(4-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl4-hydroxy-phenyl)-methanone

Product 1

HCID 101223534-{4-[2-(4-Bromo-benzyl)4,5-dimethyl-furan-3-carbonyl]-2-cyclopentyl-phenoxysulfonyl}-2-hydroxy-benzoic acidYield 75.5%

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-cyclopentyl-4-hydroxy-phenyl)-methanone (0.203 g, 0.448 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.319 g, 1.34 mmol). Purification on Dynamax C18 (85% CH3CN/H2O) gave 0.221 g (49%) of the title compound as a brown solid, mp 188-192° C. 1H NMR (DMSO-d6) δ 1.26-1.32 (m, 2H), 1.49-1.57 (m, 2H), 1.64-1.74 (m, 4H), 1.77 (s, 3H), 2.18 (s, 3H), 2.96 (quintet, 1H), 3,79 (s, 2H), 6.96 (d, 2H), 7.23 (d, 1H), 7.36-7.43 (m, 4H), 7.53-7.56 (m, 2H), 8.00 (d, 1H). IR (KBr) 3400, 2950, 1690, 1390 and 1190 cm−1. mass spectrum (−ESI) m/z 651 (M−H). Anal. Calcd. for C32H29BrO8 S: C, 58.81; H, 4.47; N, 0.00. Found: C, 58.45; H, 4.54; N, 0.07.

Workup

  1. customThe title compound was prepared
  2. customPurification on Dynamax C18 (85% CH3CN/H2O)

Sources & evidence

ORD record
ord-384718ae7bd942dab93255b8e088ee38
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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