4-Methylphenyl isocyanate → (R)-Methyl 3-methyl-2-(3-(4-(3-p-tolylureido)phenyl)isoxazole-5-carbothioamido)butanoate
Reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1)=[C:2]=[O:3].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:22]=[C:21]([C:23](=[S:33])[NH:24][C@H:25]([CH:30]([CH3:32])[CH3:31])[C:26]([O:28][CH3:29])=[O:27])[O:20][N:19]=2)=[CH:14][CH:13]=1>>[CH3:32][CH:30]([CH3:31])[C@@H:25]([NH:24][C:23]([C:21]1[O:20][N:19]=[C:18]([C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:2]([NH:1][C:4]3[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=3)=[O:3])=[CH:13][CH:14]=2)[CH:22]=1)=[S:33])[C:26]([O:28][CH3:29])=[O:27]Participants
3
Procedure
The title compound was prepared according to the procedure as set, forth in example 151, except that 1-isocyanato-4-methylbenzene was used in place of 1-fluoro-3-isocyanatobenzene and (R)-methyl 2-(3-(4-aminophenyl)isoxazole-5-carbothioamido)-3-methylbutanoate was used in place of methyl 2-(3-(4-aminophenyl)isoxazole-5-carboxamido)-3-methylbutanoate to yield 65% of the title compound. MS (ESI): m/z 467(M+H); 1HNMR (DMSO-d6, 300 MHz): δ 10.924 (d, 1H), 8.902 (s, 1H), 8.630 (s, 1H), 7.865 (d, 2H), 7.607(d, 3H), 7.351(d, 2H), 7.094(d, 2H), 4.810 (s, 1H), 3.665(s, 3H), 2.489 (m, 1H), 2.367(s, 3H), 1.033(m, 6H).