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Hydrochloric Acid → 4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-benzoic acid

HRID 2235164
ノート
印刷プレビュー

反応式

HRID 2235164 の反応式
C([O:3][C:4](=[O:35])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[CH:19][N:20]3[S:23]([C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=3[O:33][CH3:34])(=[O:25])=[O:24])=[CH:16][CH:15]=2)=[O:13])=[CH:7][CH:6]=1)C.[Li+].[OH-].Cl>O1CCCC1.CO.O>[Cl:32][C:30]1[CH:29]=[CH:28][C:27]([O:33][CH3:34])=[C:26]([S:23]([N:20]2[C:21]3[C:17](=[CH:16][CH:15]=[C:14]([C:12]([NH:11][C:8]4[CH:9]=[CH:10][C:5]([C:4]([OH:35])=[O:3])=[CH:6][CH:7]=4)=[O:13])[CH:22]=3)[CH:18]=[CH:19]2)(=[O:25])=[O:24])[CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 588317454-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-benzoic acid ethyl ester

生成物 1

HCID 160508144-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-benzoic acid

試薬・触媒・溶媒 3

HCID 887Methanol溶媒
HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-benzoic acid ethyl ester (70 mg, 0.14 mmol) in tetrahydrofuran (1.5 ml) and methanol (0.5 ml) was treated with a 1N solution of LiOH in water (0.5 ml). The mixture was stirred at room temperature for 4 hours, then acidified with 1N HCl (0.5 ml). Methanol and tetrahydrofuran were evaporated and the residual slurry was extracted three times with ethyl acetate. The combined organic phases were dried with Na2SO4 and evaporated, and the residue purified by flash chromatography (dichloromethane/methanol gradient), to yield 4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-benzoic acid as a light yellow solid, 17 mg (25%). MS (ISP): m/e=483.0 (M−H); δH (300 MHz; d6-DMSO) 12.77 (1H, bs), 10.60 (1H, s), 8.34 (1H, s), 8.08 (1H, d), 7.91-7.97 (6H, m), 7.75-7.80 (2H, m), 7.23 (1H, d), 6.91 (1H, d), 3.70 (3H, s).

後処理

  1. customMethanol and tetrahydrofuran were evaporated
  2. extractionthe residual slurry was extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried with Na2SO4
  4. customevaporated
  5. customthe residue purified by flash chromatography (dichloromethane/methanol gradient)

出典と根拠

ORDレコード
ord-e08451a94a9142e7ab8dc5d783b4b6fb
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07713996B2

反応ノート

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