Hydrochloric Acid → [2-(4-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-2-methyl-phenyl)-thiazol-4-yl]-acetic Acid

HRID 546946Notes

Reaction equation

HRID 546946 reaction equation
[OH-].[Na+].O.C([O:6][C:7](=[O:45])[CH2:8][C:9]1[N:10]=[C:11]([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])[S:12][CH:13]=1)C.Cl>CO>[CH2:21]([C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:11]2[S:12][CH:13]=[C:9]([CH2:8][C:7]([OH:45])=[O:6])[N:10]=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 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 57454139[2-(4-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-2-methyl-phenyl)-thiazol-4-yl]-acetic Acid Ethyl Ester

Product 1

HCID 15942127[2-(4-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-2-methyl-phenyl)-thiazol-4-yl]-acetic AcidYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixed solution of a 6 N sodium hydroxide aqueous solution (0.11 mL) with water (0.033 mL) was added to a solution of [2-(4-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-2-methyl-phenyl)-thiazol-4-yl]-acetic acid ethyl ester (Example 76-(1); 9.7 mg, 0.016 mmol) in methanol (0.22 mL) at room temperature, and the mixture was stirred at room temperature for 6.5 hours. The mixture was acidified with dilute hydrochloric acid aqueous solution, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by preparative TLC (dichloromethane:methanol=10:1) to give the title compound (8.8 mg, 94%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by preparative TLC (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-3ad79d30116a41c99881b5dafd0457b0
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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