Hydrochloric Acid → HCID 15942126, compound

HRID 546944Notes

Reaction equation

HRID 546944 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:45])[CH2:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH2:42][CH3:43])([C:23]3[CH:28]=[CH:27][C:26](/[CH:29]=[CH:30]/[C:31]([OH:40])([C:36]([F:39])([F:38])[F:37])[C:32]([F:35])([F:34])[F:33])=[C:25]([CH3:41])[CH:24]=3)[CH2:21][CH3:22])=[CH:16][C:15]=2[CH3:44])[CH:13]=1)C.Cl>CO.O>[CH2:21]([C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:12]2[CH:13]=[C:8]([CH2:7][C:6]([OH:45])=[O:5])[CH:9]=[N:10][CH:11]=2)=[C:15]([CH3:44])[CH:16]=1)([C:23]1[CH:28]=[CH:27][C:26](/[CH:29]=[CH:30]/[C:31]([OH:40])([C:36]([F:37])([F:38])[F:39])[C:32]([F:34])([F:35])[F:33])=[C:25]([CH3:41])[CH:24]=1)[CH2:42][CH3:43])[CH3:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57454138HCID 57454138, compound

Product 1

HCID 15942126HCID 15942126, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A 6 N sodium hydroxide aqueous solution (0.009 mL) was added to a solution of [5-(4-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic acid ethyl ester (Example 75-(1); 5.0 mg, 0.0084 mmol) in methanol (0.3 mL) and water (0.030 mL), and the mixture was stirred for two hours. 2 N hydrochloric acid aqueous solution and water were added to the reaction mixture, followed by extraction with diethyl ether and ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by thin layer silica gel chromatography (dichloromethane/methanol=5/1) to give the title compound (3.0 mg, 60%).

Workup

  1. extractionfollowed by extraction with diethyl ether and ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by thin layer silica gel chromatography (dichloromethane/methanol=5/1)

Sources & evidence

ORD record
ord-d8149e765bb540cdb7d3e2d4d0716b73
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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