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

HRID 1954274Notes

Reaction equation

HRID 1954274 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

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 5462737Magnesium diiodideHCID 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.

Workup

  1. customwas prepared
  2. customPurification on 2% H3PO4 /MeOH
  3. additiontreated silica gel
  4. washeluting with a 10 & 30% EtOAc/pet. ether step gradient

Sources & evidence

ORD record
ord-660b95d04843407aa0e2d2adbda9b1c5
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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