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 730208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 730208
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

Komponenten

5

Edukt 1

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

Produkt 1

HCID 116060383-[2-(Benzo[b]thiophene-2-sulfonylamino)-phenylsulfamoyl]-4-methoxybenzoic acidAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ad84186ff70c4a11959914956cc05210
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582673B2

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