Hydrochloric Acid → 3-Methyl-2-(5-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)thiazole-2-carboxamido)butanoic acid
Reaction equation
[CH3:1][CH:2]([CH3:36])[CH:3]([NH:8][C:9]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)=[O:24])=[CH:18][CH:17]=2)=[CH:14][N:15]=1)=[O:10])[C:4]([O:6]C)=[O:5].O.[OH-].[Li+].Cl>C1COCC1>[CH3:1][CH:2]([CH3:36])[CH:3]([NH:8][C:9]([C:11]1[S:12][C:13]([C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:33])[F:35])[CH:27]=3)=[O:24])=[CH:20][CH:21]=2)=[CH:14][N:15]=1)=[O:10])[C:4]([OH:6])=[O:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 3-methyl-2-(5-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl) thiazole-2-carboxamido)butanoate (Example 9, 100 mg) in THF (2 ml) was added 1 M aqueous solution of Lithium hydroxide monohydrate (0.38 ml) and the mixture was stirred at RT for 4 hours. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. The organic layer was separated, dried over Na2SO4, concentrated under reduced pressure and then crystallized in EtOAc to give the title compound. Yield: 60 mg (62%); 1H NMR (DMSO-d6, 300 MHz): δ 12.97 (bs, 1H), 9.18 (s, 1H), 9.13 (s, 1H), 8.37 (d, 1H), 8.36 (s, 1H), 8.03 (d, 1H), 7.71 (d, 2H), 7.61 (d, 2H), 7.55 (dd, 1H), 7.5 (dd, 1H), 7.34 (d, 1H), 4.31, (m, 1H), 2.28 (m, 1H), 0.95 (d, 6H); MS (ES+): m/z 507 (M+1).
Workup
- extractionextracted with EtOAc
- customThe organic layer was separated
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customcrystallized in EtOAc
Sources & evidence
- ORD record
- ord-1ad75c0e75ca439db309cbefece62d77
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722901B2
Reaction notes
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