Sodium Bicarbonate → (4-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetic Acid 2-(toluene-4-sulfonyl)ethyl Ester

HRID 2182849Notes

Reaction equation

HRID 2182849 reaction equation
[C:1]1([CH3:53])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][CH2:11][O:12][C:13](=[O:52])[CH2:14][O:15][C:16]2[CH:21]=[C:20](C)[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][C:47]([F:50])([F:49])[F:48])[CH:41]=[CH:40][N:39]=3)=[O:36])(=[O:25])=[O:24])=[C:18](C)[CH:17]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+]>C1COCC1.O>[C:1]1([CH3:53])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][CH2:11][O:12][C:13](=[O:52])[CH2:14][O:15][C:16]2[CH:17]=[CH:18][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][C:47]([F:50])([F:48])[F:49])[CH:41]=[CH:40][N:39]=3)=[O:36])(=[O:24])=[O:25])=[CH:20][CH:21]=2)(=[O:8])=[O:9])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 20786417HCID 20786417, compound2×

Product 1

HCID 20786423(4-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetic Acid 2-(toluene-4-sulfonyl)ethyl EsterYield 72%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of (3,5-dimethyl-4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 14, 400 mg, 0.50 mmol) and NaHCO3 (51 mg, 0.60 mmol, 1.2 eq) in THF-H2O (6 mL-3 mL) was heated to 70° C. for 3 h. Then volatile materials were removed, the residual gummy oil was dissolved in THF and the mixture was filtered to remove un-dissolved solid. The filtrate was dried, the solvent was removed by evaporation to give a yellow foam which was treated with ether-EtOAc (5:1) to precipitate a solid. The solid was treated with CH3CN, and then collected by filtration to give Compound 5 (230 mg, 72%) as a light yellow solid.

Workup

  1. customThen volatile materials were removed
  2. dissolutionthe residual gummy oil was dissolved in THF
  3. filtrationthe mixture was filtered
  4. customto remove
  5. dissolutionun-dissolved solid
  6. customThe filtrate was dried
  7. customthe solvent was removed by evaporation
  8. customto give a yellow foam which
  9. customto precipitate a solid
  10. additionThe solid was treated with CH3CN
  11. filtrationcollected by filtration

Sources & evidence

ORD record
ord-fcbf0a5be5e44cf48ebe6fef213d1516
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

Loading…