HCID 18682370, compound → 3-(3-Isobutyl-2-oxo-4-{[4-(3-o-tolyl-ureido)-phenyl]-acetyl}-piperazin-1-yl)-butyric acid
Reaction equation
C[O:2][C:3](=[O:38])[CH2:4][CH:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13](=[O:32])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:31])=[O:23])=[CH:17][CH:16]=2)[CH:9]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:8]1=[O:37])[CH3:6]>[OH-].[Na+].C(O)(C)(C)C>[CH2:33]([CH:9]1[N:10]([C:13](=[O:32])[CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:31])=[O:23])=[CH:19][CH:20]=2)[CH2:11][CH2:12][N:7]([CH:5]([CH3:6])[CH2:4][C:3]([OH:38])=[O:2])[C:8]1=[O:37])[CH:34]([CH3:36])[CH3:35]Participants
4
Procedure
A solution of 3-(3-isobutyl-2-oxo-4-{[4-(3-o-tolyl-ureido)-phenyl]-acetyl}-piperazin-1-yl)-butyric acid methyl ester (20 mg, 0.038 mmol) in a mixture of 1 ml of 0.1 N NaOH and 1 ml of tert-butanol was stirred for 16 hrs at room temperature. The reaction mixture was then concentrated under reduced pressure, dissolved in water (5 ml) and extracted with ether (5 ml×2). The aqueous portion was then acidified to pH<3 with 1N HCl and extracted with ethyl acetate. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give 16 mg of the title compound as a yellow sticky oil. MS [M+1]+509.3; 1H nmr (400 MHz, CD3OD) δ0.88-1.70 (m, 12H), 2.25 (s, 3H), 2.34-4.96 (m, 10H), 6.98 (t, J=7.4 Hz, 1H), 7.11-7.40 (m, 6H), 7.59 (d, J=7.5 Hz, 1).