Sodium Bicarbonate → HCID 69557930, compound

HRID 2182848Notes

Reaction equation

HRID 2182848 reaction equation
C1(C)C=CC(S(CC[O:12][C:13](=[O:52])[CH:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([N:27]3[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[N:29]=[C:28]3[S:36]([CH2:38][C:39]3[C:44]([CH3:45])=[C:43]([O:46][CH2:47][C:48]([F:51])([F:50])[F:49])[CH:42]=[CH:41][N:40]=3)=[O:37])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[CH2:15][CH3:16])(=O)=O)=CC=1.C([O-])(O)=O.[Na+:58]>CC#N.O>[Na+:58].[CH3:45][C:44]1[C:39]([CH2:38][S:36]([C:28]2[N:27]([S:24]([C:21]3[CH:22]=[CH:23][C:18]([O:17][CH:14]([CH2:15][CH3:16])[C:13]([O-:52])=[O:12])=[CH:19][CH:20]=3)(=[O:25])=[O:26])[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[N:29]=2)=[O:37])=[N:40][CH:41]=[CH:42][C:43]=1[O:46][CH2:47][C:48]([F:50])([F:49])[F:51]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 60028379HCID 60028379, compound2×

Product 1

HCID 69557930HCID 69557930, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A solution of 2-(4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzoimidazole-1-sulfonyl}phenoxy)butyric acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 11, 400 mg, 0.50 mmol) and NaHCO3 (47 mg, 0.55 mmol, 1.1 eq) in CH3CN-H2O (7 mL-3 mL) was heated to 70° C. for 3 h. Then volatile materials were removed by evaporation and the residual gummy oil was dissolved in CH3CN. The CH3CN solution was filtered to remove un-dissolved solids. The filtrate was dried and the residual yellow foam was treated with ether-EtOAc (5:1) to precipitate a solid. The solid was again treated with CH3CN, and the CH3CN solution was filtered to give 180 mg (58%) of 2-(4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)butyric acid sodium salt (Compound 4 sodium salt). The sodium salt was dissolved in water, and acidified to pH 3 by 1 N HCl solution, and extracted with dichloromethane. The dichloromethane layer was evaporated to give Compound 4 as a free acid, which was further purified on a short silica gel column to yield 125 mg of 2-(4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]benzimidazole-1-sulfonyl}phenoxy)butyric acid (Compound 4).

Workup

  1. customThen volatile materials were removed by evaporation
  2. dissolutionthe residual gummy oil was dissolved in CH3CN
  3. filtrationThe CH3CN solution was filtered
  4. customto remove
  5. dissolutionun-dissolved solids
  6. customThe filtrate was dried
  7. additionthe residual yellow foam was treated with ether-EtOAc (5:1)
  8. customto precipitate a solid
  9. additionThe solid was again treated with CH3CN
  10. filtrationthe CH3CN solution was filtered

Sources & evidence

ORD record
ord-2c47024ef35040db870a543b7294478b
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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