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Lansoprazole → 3-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}benzoic Acid 2-(3-nitro-benzenesulfonyl)ethyl Ester

HRID 2182840
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HRID 2182840 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+].S(Cl)(Cl)(=O)=O.[N+:33]([C:36]1[CH:37]=[C:38]([S:42]([CH2:45][CH2:46][O:47][C:48](=[O:59])[C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([S:55](Cl)(=[O:57])=[O:56])[CH:50]=2)(=[O:44])=[O:43])[CH:39]=[CH:40][CH:41]=1)([O-:35])=[O:34]>C(Cl)Cl.O>[N+:33]([C:36]1[CH:37]=[C:38]([S:42]([CH2:45][CH2:46][O:47][C:48](=[O:59])[C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([S:55]([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:57])=[O:56])[CH:50]=2)(=[O:43])=[O:44])[CH:39]=[CH:40][CH:41]=1)([O-:35])=[O:34]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 3883LansoprazoleHCID 24648Sulfuryl chlorideHCID 24758Sodium hydrideHCID 713766552-(3-Nitrobenzene-1-sulfonyl)ethyl 3-(chlorosulfonyl)benzoate

생성물 1

HCID 207863723-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}benzoic Acid 2-(3-nitro-benzenesulfonyl)ethyl Ester수율 80%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a heterogeneous mixture of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]-1H-benzimidazole (600 mg, 1.62 mmol) in CH2Cl (10 mL) was added NaH (45 mg, 1.95 mmol) at room temperature, resulting in a clear solution. To this clear mixture was added the sulfonyl chloride (Intermediate 1, 845 mg, 1.95 mmol, 1.2 eq), in CH2Cl2 at room temperature, and then the mixture was stirred for 2 h. Thereafter water was added and the mixture was extracted with CH2Cl2, and the organic layers were dried and concentrated. The residual oil was purified by column chromatography (3% MeOH in CH2Cl2) to yield 1.0 g (80%) of yellow foam.

후처리

  1. customresulting in a clear solution
  2. extractionthe mixture was extracted with CH2Cl2
  3. customthe organic layers were dried
  4. concentrationconcentrated
  5. customThe residual oil was purified by column chromatography (3% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-e12dc1e5a2e5496ca4cf0840e0f664fa
출처 데이터셋
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06897227B2

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