Trifluoroacetic acid → 2-methyl-2-({4-[2-({1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}oxy)ethyl]-1,3-thiazol-2-yl}thio)propionic acid

HRID 914345Notes

Reaction equation

HRID 914345 reaction equation
C([O:5][C:6](=[O:34])[C:7]([CH3:33])([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][O:17][C:18]2[CH:19]=[N:20][N:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[CH:22]=2)[N:14]=1)[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:33][C:7]([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][O:17][C:18]2[CH:19]=[N:20][N:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:30])[F:31])[CH:24]=3)[CH:22]=2)[N:14]=1)([CH3:8])[C:6]([OH:34])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 597588922-methyl-2-({4-[2-({1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}oxy)ethyl]-1,3-thiazol-2-yl}thio)propionic acid tert-butyl ester

Product 1

HCID 597592522-methyl-2-({4-[2-({1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}oxy)ethyl]-1,3-thiazol-2-yl}thio)propionic acidYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methyl-2-({4-[2-({1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}oxy)ethyl]-1,3-thiazol-2-yl}thio)propionic acid tert-butyl ester (400 mg) obtained in Example 158-1 was dissolved in dichloromethane (6 mL), trifluoroacetic acid (2 mL) was added, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1 to 0:1) to give the title compound (290 mg) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1 to 0:1)

Sources & evidence

ORD record
ord-9b48129e1cc3460e97563e4c65b3de9e
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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