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

HRID 914435Notes

Reaction equation

HRID 914435 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][N:18]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:28]([N:18]([C:19]1[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=1)[CH2:17][CH2:16][C:14]1[N:15]=[C:11]([S:10][C:7]([CH3:9])([CH3:8])[C:6]([OH:35])=[O:5])[S:12][CH:13]=1)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 597588452-[(4-{2-[Heptyl(4-nitrophenyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

Product 1

HCID 597589072-[(4-{2-[Heptyl(4-nitrophenyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acidYield 60.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(4-{2-[Heptyl(4-nitrophenyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (200 mg) obtained in Example 303-3 was dissolved in dichloromethane (5 mL), trifluoroacetic acid (5 mL) was added, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, and hexane was added to the residue to give the title compound (108 mg) as a pale-yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and hexane
  2. additionwas added to the residue

Sources & evidence

ORD record
ord-1cc3ba31716e473c85155cfc913d4083
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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