Acetic Anhydride → 2-Acetoxy-4-[4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxysulfonyl]-benzoic acid

Reaction equation

[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:36]=[CH:35][C:20]([O:21][S:22]([C:25]3[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[C:27]([OH:34])[CH:26]=3)(=[O:24])=[O:23])=[C:19]([CH:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)[CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[C:42](OC(=O)C)(=[O:44])[CH3:43].[I-].[Mg+2].[I-]>>[C:42]([O:34][C:27]1[CH:26]=[C:25]([S:22]([O:21][C:20]2[CH:35]=[CH:36][C:17]([C:9]3[C:10]4[C:14]([CH3:15])=[C:13]([CH3:16])[S:12][C:11]=4[C:2]([Br:1])=[C:3]4[C:8]=3[CH:7]=[CH:6][CH:5]=[CH:4]4)=[CH:18][C:19]=2[CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)(=[O:24])=[O:23])[CH:33]=[CH:32][C:28]=1[C:29]([OH:31])=[O:30])(=[O:44])[CH3:43]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 5462737Magnesium diiodide

HCID 98958444-[4-(9-Bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxysulfonyl]-2-hydroxy-benzoic acid

Product 1

HCID 99180302-Acetoxy-4-[4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxysulfonyl]-benzoic acidYield 79%

Procedure

Using 4-[4-(9-Bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxysulfonyl]-2-hydroxy-benzoic acid (0.293 g, 0.450 mmol), acetic anhydride (3.6 mL, 38.2 mmol) and magnesium iodide (0.125 g, 0.450 mmol) the tidle compound was prepared according to the procedure in Example 5. Purification on 2% H3PO4 /MeOH treated silica gel, eluting with a 10 & 30% EtOAc/pet. ether step gradient gave 0.245 g (79%) of the title compound as a colorless solid, mp 155-167° C.; 1H NMR (DMSO-d6) δ 1.32-1.38 (m, 2 H), 1.49-1.53 (m, 5 H), 1.58-1.63 (m, 3 H), 1.78-1.80 (m, 1 H), 2.30 (s, 3 H), 2.45 (s, 3 H), 3.00-3.28 (m, 1 H), 7.25-7.29 (m, 2 H), 7.36-7.39 (m, 2 H), 7.50 (t, 1 H), 7.67 (t, 1 H), 7.83 (d, b 1 H), 7.93 (dd, 1 H), 8.19-8.22 (m, 2 H), 13.6-13.8 (br. s, 1 H). mass spectrum (-ESI), m/z 691/693 (M-H). Anal. Calcd. for C34H29BrO7S2.0.3H2O: C, 58.42; H, 4.27 N, 0.00. Found: C, 58.38; H, 4.55 N, 0.10.