Water → (2-(2-Benzenesulfonyl-ethoxycarbonylmethoxy)-4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetic Acid 2-benzenesulfonyl-ethyl Ester

HRID 2182864Notes

Reaction equation

HRID 2182864 reaction equation
[CH3:1][C:2]1[C:3]([CH2:14][S:15]([C:17]2[NH:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=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+].[C:28]1([S:34]([CH2:37][CH2:38][O:39][C:40](=[O:69])[CH2:41][O:42][C:43]2[CH:48]=[CH:47][C:46]([S:49](Cl)(=[O:51])=[O:50])=[CH:45][C:44]=2[O:53][CH2:54][C:55]([O:57][CH2:58][CH2:59][S:60]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)(=[O:62])=[O:61])=[O:56])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>C(Cl)Cl>[C:28]1([S:34]([CH2:37][CH2:38][O:39][C:40](=[O:69])[CH2:41][O:42][C:43]2[CH:48]=[CH:47][C:46]([S:49]([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:50])=[O:51])=[CH:45][C:44]=2[O:53][CH2:54][C:55]([O:57][CH2:58][CH2:59][S:60]([C:63]2[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=2)(=[O:62])=[O:61])=[O:56])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3883LansoprazoleHCID 24758Sodium hydrideHCID 20786399[2-(2-Benzenesulfonyl-ethoxycarbonylmethoxy)-4-chlorosulfonyl-phenoxy]-acetic acid 2-benzenesulfonyl-ethyl ester2×

Product 1

HCID 20786400(2-(2-Benzenesulfonyl-ethoxycarbonylmethoxy)-4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetic Acid 2-benzenesulfonyl-ethyl EsterYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a heterogeneous mixture of 2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)pyridin-2-ylmethanesulfinyl]-benzimidazole, (LANSOPRAZOLE) (500 mg, 1.35 mmol) in CH2Cl2 (10 mL) was added NaH (40 mg, 1.63 mmol) at room temperature resulting in a clear solution. To this clear mixture was added [2-(2-benzenesulfonyl-ethoxycarbonylmethoxy)-4-chlorosulfonyl-phenoxy]-acetic acid 2-benzenesulfonyl-ethyl ester (Intermediate 29, 1.0 g, 1.63 mmol, 1.2 eq) in CH2Cl2 (5 mL) at room temperature, and the mixture was stirred for 3 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 2% MeOH in CH2Cl2) to yield Intermediate 30 (1.05 g, 78%) as an off-white foam.

Workup

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

Sources & evidence

ORD record
ord-865d971cf70340f3a8e6d4556f44ec99
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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