Trifluoroacetic acid → 2-Methyl-2-{[4-(2-oxo-2-{[4'-(trifluoromethyl)biphenyl-4-yl]amino}ethyl)-1,3-thiazol-2-yl]thio}propionic acid

HRID 914386Notes

Reaction equation

HRID 914386 reaction equation
C([O:5][C:6](=[O:36])[C:7]([CH3:35])([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][C:16](=[O:34])[NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[N:14]=1)[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:35][C:7]([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][C:16](=[O:34])[NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[N:14]=1)([CH3:8])[C:6]([OH:36])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 597589402-Methyl-2-{[4-(2-oxo-2-{[4'-(trifluoromethyl)biphenyl-4-yl]amino}ethyl)-1,3-thiazol-2-yl]thio}propionic acid tert-butyl ester

Product 1

HCID 597590132-Methyl-2-{[4-(2-oxo-2-{[4'-(trifluoromethyl)biphenyl-4-yl]amino}ethyl)-1,3-thiazol-2-yl]thio}propionic acidYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methyl-2-{[4-(2-oxo-2-{[4′-(trifluoromethyl)biphenyl-4-yl]amino}ethyl)-1,3-thiazol-2-yl]thio}propionic acid tert-butyl ester (540 mg) obtained in Example 458-2 was dissolved in dichloromethane (10 mL), trifluoroacetic acid (4 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 white solid.

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-2922b564b41d4740b7f20b49e3e5d5d7
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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