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

HRID 2182847Notes

Reaction equation

HRID 2182847 reaction equation
C1(C)C=CC(S(CC[O:12][C:13](=[O:50])[C:14]2[CH:19]=[C:18]([S:20]([N:23]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[N:25]=[C:24]3[S:32]([CH2:34][C:35]3[C:40]([CH3:41])=[C:39]([O:42][CH2:43][C:44]([F:47])([F:46])[F:45])[CH:38]=[CH:37][N:36]=3)=[O:33])(=[O:22])=[O:21])[CH:17]=[CH:16][C:15]=2[O:48][CH3:49])(=O)=O)=CC=1.C([O-])(O)=O.[Na+:56].O.CC(O)C>CC#N>[Na+:56].[CH3:49][O:48][C:15]1[CH:16]=[CH:17][C:18]([S:20]([N:23]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[N:25]=[C:24]2[S:32]([CH2:34][C:35]2[C:40]([CH3:41])=[C:39]([O:42][CH2:43][C:44]([F:46])([F:47])[F:45])[CH:38]=[CH:37][N:36]=2)=[O:33])(=[O:22])=[O:21])=[CH:19][C:14]=1[C:13]([O-:50])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 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 ester2×

Product 1

HCID 207864082-Methoxy-5-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]benzimidazole-1-sulfonyl}-benzoic acid sodium saltYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture 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, 400 mg, 0.52 mmol) and NaHCO3 (52 mg, 0.62 mmol, 1.2 eq) in CH3CN (3 mL)-H2O (2 mL)-i-PrOH (1 mL) was heated to 70° C. for 1.5 h. Then volatile materials were removed by evaporation and the residual oil was dissolved in CH2Cl2-MeOH, the mixture was filtered to remove insoluble solids. The filtrate was concentrated by evaporation. The residual syrup was dissolved in H2O, and the mixture was extracted with CH2Cl2 (2 times) to remove the starting material, lansoprazole and tolyl vinyl sulfone. The water solution was freeze-dried to yield 200 mg (65%) Compound 3 sodium salt as a light yellow solid.

Workup

  1. customThen volatile materials were removed by evaporation
  2. dissolutionthe residual oil was dissolved in CH2Cl2-MeOH
  3. filtrationthe mixture was filtered
  4. customto remove insoluble solids
  5. concentrationThe filtrate was concentrated by evaporation
  6. dissolutionThe residual syrup was dissolved in H2O
  7. extractionthe mixture was extracted with CH2Cl2 (2 times)
  8. customto remove the starting material, lansoprazole and tolyl vinyl sulfone
  9. dry with materialThe water solution was freeze-dried

Sources & evidence

ORD record
ord-192485371eab4de4bf01e484ba717ed7
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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