Sodium Bicarbonate → 3-{2-[4-(3-Methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}-4-methylbenzoic acid sodium salt

HRID 2182877Notes

Reaction equation

HRID 2182877 reaction equation
C1(C)C=CC(S(CC[O:12][C:13](=[O:49])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([S:21]([N:24]3[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[N:26]=[C:25]3[S:33]([CH2:35][C:36]3[C:41]([CH3:42])=[C:40]([O:43][CH2:44][CH2:45][CH2:46][O:47][CH3:48])[CH:39]=[CH:38][N:37]=3)=[O:34])(=[O:23])=[O:22])[CH:15]=2)(=O)=O)=CC=1.C([O-])(O)=O.[Na+:55]>CC#N.O>[Na+:55].[CH3:48][O:47][CH2:46][CH2:45][CH2:44][O:43][C:40]1[CH:39]=[CH:38][N:37]=[C:36]([CH2:35][S:33]([C:25]2[N:24]([S:21]([C:16]3[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=3[CH3:20])[C:13]([O-:49])=[O:12])(=[O:23])=[O:22])[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[N:26]=2)=[O:34])[C:41]=1[CH3:42]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 207864393-{2-[4-(3-Methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}-4-methylbenzoic acid 2-(toluene-4-sulfonyl)ethyl ester2×

Product 1

HCID 207864663-{2-[4-(3-Methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}-4-methylbenzoic acid sodium saltYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To the solution of 3-{2-[4-(3-methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}-4-methylbenzoic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 53, 1.5 g, 1.97 mmol) in 15 mL of CH3CN was added a solution of NaHCO3 (200 mg, 2.36 mmol, 1.2 eq) in 7 mL of H2O at room temperature, and then the mixture was heated to 65° C. for 2 h. Thereafter most of the CH3CN was removed, the mixture was extracted with EtOAc, and the aqueous layer was lyophilized overnight. The solid was dissolved in CH2Cl2, and then the mixture was filtered to remove insoluble solids. The filtrate was concentrated to near dryness. The residual oil was dissolved in about 2 mL of CH2Cl2 and EtOAc-hexane (7:1) was added to precipitate a white solid. The precipitate was collected by filtration, washed with EtOAc-hexane (7:1), and dried under vacuum to give 950 mg (80%) of 3-{2-[4-(3-methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}-4-methylbenzoic acid sodium salt (Compound 28) as a white solid.

Workup

  1. customThereafter most of the CH3CN was removed
  2. extractionthe mixture was extracted with EtOAc
  3. dissolutionThe solid was dissolved in CH2Cl2
  4. filtrationthe mixture was filtered
  5. customto remove insoluble solids
  6. concentrationThe filtrate was concentrated
  7. dissolutionThe residual oil was dissolved in about 2 mL of CH2Cl2
  8. additionEtOAc-hexane (7:1) was added
  9. customto precipitate a white solid
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with EtOAc-hexane (7:1)
  12. customdried under vacuum

Sources & evidence

ORD record
ord-724891dad00a40d0b4299830c4c668ab
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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