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

HRID 1067369Notes

Reaction equation

HRID 1067369 reaction equation
[Br:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][C:5]1[O:6][C:7]([CH3:25])=[C:8]([CH3:24])[C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:13]=1)=[O:11].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][CH:27]=[CH:26][C:3]=1[CH2:4][C:5]1[O:6][C:7]([CH3:25])=[C:8]([CH3:24])[C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][S:31]([C:34]2[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[C:36]([OH:43])[CH:35]=2)(=[O:33])=[O:32])=[C:14]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:13]=1)=[O:11]

Participants

3

Reactant 2

HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acidHCID 23445646[2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl-4-hydroxy-phenyl)-methanone

Product 1

HCID 101223524-{4-[2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-carbonyl]-2-cyclopentyl-phenoxysulfonyl}-2-hydroxy-benzoic AcidYield 68.3%

Procedure

The title compound was prepared according to the procedure in Example 4 using [2-(2-bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl-4-hydroxy-phenyl)-methanone (0.516 g, 1.14 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.540 g, 2.28 nmmol). Purification on 2% H3PO4/MeOH treated silica gel, eluting with a 15 & 25% EtOAc/hexane step gradient gave 0.509 g (68%) of the title compound as a brown solid, mp 72-82° C. 1H NMR (DMSO-d6) δ1.25-1.34 (m, 2H), 1.50-1.55 (m, 2H), 1.62-1.74 (m, 4H), 1.77 (s, 3H), 2.15 (s, 3H), 2.95 (quintet, 1H), 3.88 (s, 2H), 7.10-7.15 (m, 2H), 7.20 (d, 1H), 7.27 (t, 1H), 7.35-7.37 (m, 2H), 7.48-7.58 (m, 3H), 7.96 (dd, 1H). IR (KBr) 3400,2950, 1690, 1390 and 1190 cm−1. mass spectrum (−ESI) m/z 651 (M−H). Anal. Calcd. for C32H29BrO8S.0.4H2O: C, 58.17; H, 4.55; N, 0.00. Found: C, 58.20; H, 4.55; N, 0.03.

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

Sources & evidence

ORD record
ord-a46d93db2f0243829f9aa8bccb976d38
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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