Lansoprazole → HCID 20786423, 화합물

HRID 2182843

반응식

HRID 2182843 반응식
[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

참가 물질

8

반응물 6

HCID 3883LansoprazoleHCID 24758Sodium hydrideHCID 516892Sodium Bicarbonate2회HCID 21989438SulfurochloridateHCID 58426230HCID 58426230, 화합물HCID 59316688HCID 59316688, 화합물

생성물 1

HCID 20786423HCID 20786423, 화합물수율 94%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-fedb963048944885a00ed1ff4b580582
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06897227B2

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