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Water → 6-[2-(4-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)acetylamino]hexanoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester

HRID 2182856
ノート
印刷プレビュー

反応式

HRID 2182856 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH2:13][CH2:14][O:15][C:16](=[O:37])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:36])[CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:38][C:39]1[C:40]([CH2:51][S:52]([C:54]2[NH:58][C:57]3[CH:59]=[CH:60][CH:61]=[CH:62][C:56]=3[N:55]=2)=[O:53])=[N:41][CH:42]=[CH:43][C:44]=1[O:45][CH2:46][C:47]([F:50])([F:49])[F:48].[H-].[Na+].O>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH2:13][CH2:14][O:15][C:16](=[O:37])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:36])[CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([N:55]3[C:56]4[CH:62]=[CH:61][CH:60]=[CH:59][C:57]=4[N:58]=[C:54]3[S:52]([CH2:51][C:40]3[C:39]([CH3:38])=[C:44]([O:45][CH2:46][C:47]([F:48])([F:49])[F:50])[CH:43]=[CH:42][N:41]=3)=[O:53])(=[O:34])=[O:33])=[CH:28][CH:27]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 3883LansoprazoleHCID 24758Sodium hydrideHCID 865925656-[2-(4-Chlorosulfonyl-phenoxy)-acetylamino]-n-hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester2 回

生成物 1

HCID 207863756-[2-(4-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)acetylamino]hexanoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester
収率 94%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

6-[2-(4-chlorosulfonyl-phenoxy)-acetylamino]-n-hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester (Intermediate 19, 1.0 g, 1.73 mmol, 1.27 eq) in CH2Cl2 (5 mL) was added to a heterogeneous mixture of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]-1H-benzimidazole (500 mg, 1.36 mmol) in CH2Cl2 (10 mL) and NaH (40 mg, 1.65 mmol) at room temperature, and the mixture was stirred for 2 h. Thereafter water was added, the mixture was extracted with CH2Cl2, and the organic layers were dried and concentrated under reduced pressure. The residual oil was purified by column chromatography (CH2Cl2 to 3% MeOH in CH2Cl2) to yield 6-[2-(4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxy)acetylamino]hexanoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester (Intermediate 20, 1.15 g, 94%) as an off-white foam.

後処理

  1. extractionthe mixture was extracted with CH2Cl2
  2. customthe organic layers were dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residual oil was purified by column chromatography (CH2Cl2 to 3% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-74b5b4c58a744b1cb858c42eca8babdc
出典データセット
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06897227B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート