Lansoprazole → HCID 20786423、化合物

HRID 2182843

反応式

HRID 2182843 の反応式
[CH3:1][C:2]1[C:3]([CH2:14][S:15]([C:17]2[NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[N:18]=2)=[O:16])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].[H-].[Na+].C1(C)C=CC(S(CCOC(=O)C)(=O)=O)=CC=1.[C:44]1([CH3:70])[CH:49]=[CH:48][C:47]([S:50]([CH2:53][CH2:54][O:55][C:56](=[O:69])[CH2:57][O:58][C:59]2[CH:64]=[CH:63][C:62]([S:65](Cl)(=[O:67])=[O:66])=[CH:61][CH:60]=2)(=[O:52])=[O:51])=[CH:46][CH:45]=1.C([O-])(O)=O.[Na+].ClS([O-])(=O)=O>C(Cl)Cl>[C:44]1([CH3:70])[CH:49]=[CH:48][C:47]([S:50]([CH2:53][CH2:54][O:55][C:56](=[O:69])[CH2:57][O:58][C:59]2[CH:64]=[CH:63][C:62]([S:65]([N:21]3[C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[N:18]=[C:17]3[S:15]([CH2:14][C:3]3[C:2]([CH3:1])=[C:7]([O:8][CH2:9][C:10]([F:13])([F:11])[F:12])[CH:6]=[CH:5][N:4]=3)=[O:16])(=[O:66])=[O:67])=[CH:61][CH:60]=2)(=[O:52])=[O:51])=[CH:46][CH:45]=1

参加物

8

反応物 6

HCID 3883LansoprazoleHCID 24758Sodium hydrideHCID 516892Sodium Bicarbonate2 回HCID 21989438SulfurochloridateHCID 58426230HCID 58426230、化合物HCID 59316688HCID 59316688、化合物

生成物 1

HCID 20786423HCID 20786423、化合物収率 94%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a heterogeneous solution of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]-1H-benzimidazole (900 mg, 2.44 mmol) in 30 mL of CH2Cl2 was added 70 mg of NaH (2.92 mmol) at room temperature, during which time the mixture became homogeneous. To this clear reaction mixture was added the 4-chlorosulfonylphenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 4, 1.26 g, 2.92 mmol, 1.2 eq). About 1 g of solid NaHCO3 was added after the chlorosulfonate has dissolved completely in the reaction mixture. (Without addition of NaHCO3 the mixture became black when the reaction was complete.) Thereafter the solvent was removed by evaporation and the residual oil was purified by column chromatography (silica gel, CH2Cl2 to 4% MeOH in CH2Cl2) to give 1.75 g (94%) of the desired product (Intermediate 5) as an off-white foam.

後処理

  1. dissolutionhas dissolved completely in the reaction mixture
  2. custom) Thereafter the solvent was removed by evaporation
  3. customthe residual oil was purified by column chromatography (silica gel, CH2Cl2 to 4% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-fedb963048944885a00ed1ff4b580582
出典データセット
uspto-grants-2005_05
特許番号
US06897227B2

関連ノート

読み込み中…