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 730208노트

반응식

HRID 730208 반응식
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

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ad84186ff70c4a11959914956cc05210
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582673B2

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