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

HRID 914303Notes

Reaction equation

HRID 914303 reaction equation
C([O:5][C:6](=[O:34])[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]([C:25]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:26])=[CH:21][CH:20]=2)[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH:27]([C:25]([C:22]1[CH:23]=[CH:24][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:34])=[O:5])[S:12][CH:13]=2)=[CH:20][CH:21]=1)=[O:26])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 597590482-[(4-{2-[4-(Anilinocarbonyl)phenoxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

Product 1

HCID 597594152-[(4-{2-[4-(Anilinocarbonyl)phenoxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acidYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(4-{2-[4-(Anilinocarbonyl)phenoxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (480 mg) obtained in Example 60-3 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 (400 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-78a947d9abbb412686f310685bd5cbee
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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