Sodium Bicarbonate → HCID 20786379, compound

HRID 2182879Notes

Reaction equation

HRID 2182879 reaction equation
C1(C)C=CC(S(CC[O:12][C:13](=[O:52])[CH2:14][O:15][C:16]2[CH:21]=[C:20]([CH3:22])[C:19]([S:23]([N:26]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[N:28]=[C:27]3[S:35]([CH2:37][C:38]3[C:43]([CH3:44])=[C:42]([O:45][CH2:46][CH2:47][CH2:48][O:49][CH3:50])[CH:41]=[CH:40][N:39]=3)=[O:36])(=[O:25])=[O:24])=[C:18]([CH3:51])[CH:17]=2)(=O)=O)=CC=1.C([O-])(O)=O.[Na+:58]>CC#N.O>[Na+:58].[CH3:22][C:20]1[CH:21]=[C:16]([CH:17]=[C:18]([CH3:51])[C:19]=1[S:23]([N:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=[C:27]1[S:35]([CH2:37][C:38]1[C:43]([CH3:44])=[C:42]([O:45][CH2:46][CH2:47][CH2:48][O:49][CH3:50])[CH:41]=[CH:40][N:39]=1)=[O:36])(=[O:24])=[O:25])[O:15][CH2:14][C:13]([O-:52])=[O:12]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 20786424HCID 20786424, compound2×

Product 1

HCID 20786379HCID 20786379, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 3,5-dimethyl-4-{2-[4-(3-methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}phenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 58, 1.6 g, 1.90 mmol) in 10 mL of CH3CN was added a solution of NaHCO3 (208 mg, 2.47 mmol, 1.3 eq) in 5 mL of H2O. The mixture was heated to 65° C. for 3 h. Thereafter all the volatile materials were removed under vacuum, the mixture was washed with EtOAc (2×), and then the aqueous layer was lyophilized overnight. The solid was dissolved in 80 mL of CH2Cl2, and then the mixture was filtered to remove insoluble material. The filtrate was concentrated and the residual oil was dissolved in 5 mL of CH2Cl2. EtOAc was added to the mixture to precipitate a white solid. The precipitate was collected by filtration, washed with EtOAc, and dried under vacuum to yield 800 mg (62%) of 3,5-dimethyl-4-{2-[4-(3-methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}phenoxyacetic acid sodium salt (Compound 33) as a white solid.

Workup

  1. customThereafter all the volatile materials were removed under vacuum
  2. washthe mixture was washed with EtOAc (2×)
  3. dissolutionThe solid was dissolved in 80 mL of CH2Cl2
  4. filtrationthe mixture was filtered
  5. customto remove insoluble material
  6. concentrationThe filtrate was concentrated
  7. dissolutionthe residual oil was dissolved in 5 mL of CH2Cl2
  8. additionEtOAc was added to the mixture
  9. customto precipitate a white solid
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with EtOAc
  12. customdried under vacuum

Sources & evidence

ORD record
ord-ccb6ffddeb0a4eb8a59f08c8f46e4f27
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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