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 2182840Notes

Reaction equation

HRID 2182840 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+].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]

Participants

7

Reactant 4

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

Product 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 EsterYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-e12dc1e5a2e5496ca4cf0840e0f664fa
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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