3-[2-(Benzo[b]thiophene-2-sulfonylamino)phenylsulfamoyl]-4-methoxybenzoic acid methyl ester → 3-[2-(Benzo[b]thiophene-2-sulfonylamino)-phenylsulfamoyl]-4-methoxybenzoic acid

HRID 730208Notes

Reaction equation

HRID 730208 reaction equation
C[O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([S:12](=[O:34])(=[O:33])[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH:20][S:21]([C:24]2[S:28][C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[CH:25]=2)(=[O:23])=[O:22])[CH:5]=1>C1COCC1.CO.[OH-].[Na+]>[S:28]1[C:24]([S:21]([NH:20][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[NH:13][S:12]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=2[O:10][CH3:11])[C:3]([OH:35])=[O:2])(=[O:33])=[O:34])(=[O:23])=[O:22])=[CH:25][C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]1=2

Participants

5

Reactant 1

HCID 116851903-[2-(Benzo[b]thiophene-2-sulfonylamino)phenylsulfamoyl]-4-methoxybenzoic acid methyl ester

Product 1

HCID 116060383-[2-(Benzo[b]thiophene-2-sulfonylamino)-phenylsulfamoyl]-4-methoxybenzoic acidYield 96.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3-[2-(Benzo[b]thiophene-2-sulfonylamino) -phenyl sulfamoyl]-4-methoxy-benzoic acid methyl ester (5 mmol, obtained as in Example 3) in THF (10 mL) and methanol (10 mL), 4 M aq. NaOH (5 mL) was added at RT. The reaction mixture was stirred at room temperature till the reaction was complete. The reaction mixture was then concentrated in vacuo and acidified with 10% aq. HCl to pH ˜3. A white precipitate was formed which was filtered, washed with ether and dried, affording 2.5 g of 3-[2-(benzo[b]thiophene-2-sulfonylamino) -phenylsulfamoyl]-4-methoxybenzoic acid. MS: 519.8 (M+1)+. 1H NMR (DMSO-d6, 400 MHz): δ 4.05 (s, 3H), 6.89 (d, 1H), 6.99 (dd, 1H), 7.11 (dd, 1H), 7.25 (d, 1H), 7.38 (d, 1H), 7.48 (dd, 1H), 7.53 (dd, 1H), 7.91 (s, 1H), 7.98 (d, 1H), 8.65 (d, 1H), 8.13 (dd, 1H), 8.16 (dd, 1H) ppm.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customA white precipitate was formed which
  3. filtrationwas filtered
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-ad84186ff70c4a11959914956cc05210
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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