Sodium Bicarbonate → HCID 131724896, compound

HRID 2182865Notes

Reaction equation

HRID 2182865 reaction equation
C1(S(CC[O:12][C:13](=[O:66])[CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([N:25]3[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[N:27]=[C:26]3[S:34]([CH2:36][C:37]3[C:42]([CH3:43])=[C:41]([O:44][CH2:45][C:46]([F:49])([F:48])[F:47])[CH:40]=[CH:39][N:38]=3)=[O:35])(=[O:24])=[O:23])=[CH:18][C:17]=2[O:50][CH2:51][C:52]([O:54]CCS(C2C=CC=CC=2)(=O)=O)=[O:53])(=O)=O)C=CC=CC=1.C([O-])(O)=O.[Na+:71]>C1COCC1.O>[Na+:71].[Na+:71].[C:52]([CH2:51][O:50][C:17]1[CH:18]=[C:19]([S:22]([N:25]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[N:27]=[C:26]2[S:34]([CH2:36][C:37]2[C:42]([CH3:43])=[C:41]([O:44][CH2:45][C:46]([F:47])([F:48])[F:49])[CH:40]=[CH:39][N:38]=2)=[O:35])(=[O:23])=[O:24])[CH:20]=[CH:21][C:16]=1[O:15][CH2:14][C:13]([O-:66])=[O:12])([OH:54])=[O:53].[C:52]([CH2:51][O:50][C:17]1[CH:18]=[C:19]([S:22]([N:25]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[N:27]=[C:26]2[S:34]([CH2:36][C:37]2[C:42]([CH3:43])=[C:41]([O:44][CH2:45][C:46]([F:47])([F:48])[F:49])[CH:40]=[CH:39][N:38]=2)=[O:35])(=[O:23])=[O:24])[CH:20]=[CH:21][C:16]=1[O:15][CH2:14][C:13]([O-:66])=[O:12])([OH:54])=[O:53]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 20786400(2-(2-Benzenesulfonyl-ethoxycarbonylmethoxy)-4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetic Acid 2-benzenesulfonyl-ethyl Ester2×

Product 1

HCID 131724896HCID 131724896, compoundYield 88.3%

Reagents, catalysts & solvents 1

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

Procedure

A solution of (2-(2-benzenesulfonyl-ethoxycarbonylmethoxy)-4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetic acid 2-benzenesulfonyl-ethyl ester (Intermediate 30, 500 mg, 0.50 mmol) and NaHCO3 (90 mg, 1.10 mmol, 2.2 eq) in THF-H2O (6 mL-3 mL) was heated to 70° C. for 2 h. Thereafter volatile materials were removed by evaporation under reduced pressure and the residual semi-solid was briefly treated with MeOH-CH2Cl2 (1:1). The resulting solid was collected by filtration to give Compound 12 (300 mg, 74%) as an off-white solid.

Workup

  1. customThereafter volatile materials were removed by evaporation under reduced pressure
  2. additionthe residual semi-solid was briefly treated with MeOH-CH2Cl2 (1:1)
  3. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-dbd012cbff2c49afb739cd2744ab0fee
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

Loading…