Water → 2-Methoxy-5-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}benzoic acid 2-(toluene-4-sulfonyl)ethyl ester

HRID 2182846Notes

Reaction equation

HRID 2182846 reaction equation
[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+].Cl[S:29]([C:32]1[CH:33]=[CH:34][C:35]([O:53][CH3:54])=[C:36]([CH:52]=1)[C:37]([O:39][CH2:40][CH2:41][S:42]([C:45]1[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=1)(=[O:44])=[O:43])=[O:38])(=[O:31])=[O:30].O>C(Cl)Cl>[C:48]1([CH3:51])[CH:49]=[CH:50][C:45]([S:42]([CH2:41][CH2:40][O:39][C:37](=[O:38])[C:36]2[CH:52]=[C:32]([S:29]([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:31])=[O:30])[CH:33]=[CH:34][C:35]=2[O:53][CH3:54])(=[O:44])=[O:43])=[CH:46][CH:47]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3883LansoprazoleHCID 24758Sodium hydrideHCID 224793622-(p-Toluenesulfonyl)ethyl 5-chlorosulfonyl-2-methoxybenzoate2×

Product 1

HCID 207864362-Methoxy-5-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}benzoic acid 2-(toluene-4-sulfonyl)ethyl esterYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a clear solution of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]-1H-benzimidazole (740 mg, 2.0 mmol) and NaH (60 mg, 2.5 mmol) in 10 mL of CH2Cl2 was added 2-(p-toluenesulfonyl)ethyl 5-chlorosulfonyl-2-methoxybenzoate (Intermediate 7, 1.0 g, 2.3 mmol). The resulting mixture was stirred at room temperature for 1.5 h. Thereafter water was added and the mixture was extracted with CH2Cl2. The dichloromethane layer was dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to give a thick oil. The oil was purified by column chromatography (silica gel, CH2Cl2 to 2% MeOH in CH2Cl2) to give 1.0 g (65%) of 2-methoxy-5-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}benzoic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 8).

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
  3. customevaporated under reduced pressure
  4. customto give a thick oil
  5. customThe oil was purified by column chromatography (silica gel, CH2Cl2 to 2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-52cd8cac649e48aa80cef716cf851179
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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