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 730208ノート

反応式

HRID 730208 の反応式
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

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ad84186ff70c4a11959914956cc05210
出典データセット
uspto-grants-2009_09
特許番号
US07582673B2

反応ノート

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