4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-[2-Cyclopentyl-4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenoxysulfonyl]-2-hydroxy-benzoic acid

HRID 1954278Notes

Reaction equation

[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]3[C:13](=[C:14]([C:15]4[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([CH:22]5[CH2:26][CH2:25][CH2:24][CH2:23]5)[CH:16]=4)[C:4]=2[C:3]=1[CH3:27])[CH:12]=[CH:11][CH:10]=[CH:9]3.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]>>[CH:22]1([C:17]2[CH:16]=[C:15]([C:14]3[C:4]4[C:3]([CH3:27])=[C:2]([CH3:1])[S:6][C:5]=4[CH:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)[CH:20]=[CH:19][C:18]=2[O:21][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])[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

Reactant 2

HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acid

HCID 184307052-Cyclopentyl-4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenol

Product 1

HCID 98295764-[2-Cyclopentyl-4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenoxysulfonyl]-2-hydroxy-benzoic acid

Procedure

Using 4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenol and 4-chlorosulphonyl-2-hydroxybenzoic acid the title compound was prepared according to the procedure in Example 1, step 9. Purification on 2% H3PO4 /MeOH treated silica gel eluting with a 0 & 10% EtOAc/hexane step gradient gave 0.66 g of the title compound as a pale yellow solid, mp 230-237° C.; 1H NMR (DMSO-d6) δ 1.30-1.35 (m, 2 H), 1.45-1.52 (m, 5 H), 1.58-1.63 (m, 3 H), 2.40 (s, 2 H), 3.05 (q, 1 H), 7.21-7.29 (m, 4 H), 7.35-7.47 (m, 4 H), 7.97 (d, 1 H), 8.03 (d, 1 H), 8.49 (s, 1 H). IR (KBr) 2950, 1675, 1390, 1190 and 850 cm-1. mass spectrum (-ESI), m/z 571 (M-H). Anal. Calcd. for C32H28O6S2.0.2H2O: C, 66.69; H, 4.97 N, 0.00. Found: C, 66.69; H, 5.01 N, 0.03.

Sources & evidence

ORD record: ord-358599b0336a4605a0495d1a31bd78d4
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121271

Reaction notes

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