Trifluoroacetic acid → 2-{[4-(2-{4-[Benzoyl(methyl)amino]phenoxy}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid

HRID 914299Notes

Reaction equation

HRID 914299 reaction equation
C([O:5][C:6](=[O:35])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]([C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH3:26])=[CH:21][CH:20]=2)[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:27]([N:25]([CH3:26])[C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH2:16][C:14]2[N:15]=[C:11]([S:10][C:7]([CH3:9])([CH3:8])[C:6]([OH:35])=[O:5])[S:12][CH:13]=2)=[CH:24][CH:23]=1)(=[O:34])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 597593902-{[4-(2-{4-[Benzoyl(methyl)amino]phenoxy}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

Product 1

HCID 597593462-{[4-(2-{4-[Benzoyl(methyl)amino]phenoxy}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acidYield 65.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-{[4-(2-{4-[Benzoyl(methyl)amino]phenoxy}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (290 mg) obtained in Example 55-1 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 (170 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-c4e24102538542698063972d68088ff1
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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