Benzyl succinimido carbonate → Benzyl (1R,2R)-2-((S)-1-(4-(oxazol-2-yl)phenyl)piperidin-3-ylamino)cyclohexylcarbamate
Reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]3[NH2:25])[CH2:13]2)=[CH:8][CH:7]=1.[C:26](=O)([O:35]N1C(=O)CCC1=O)[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH2:15][C@H:14]([NH:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]3[NH:25][C:26](=[O:35])[O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:13]2)=[CH:8][CH:7]=1Participants
Procedure
Benzyl (1R,2R)-2-((S)-1-(4-(oxazol-2-yl)phenyl)piperidin-3-ylamino)cyclohexylcarbamate was synthesized using (1R,2R)—N1-(1-(4-(oxazol-2-yl)phenyl)piperidin-3-yl)cyclohexane-1,2-diamine (from Example 15, step D) (11.58 mg, 0.034 mmol) and benzyl 2,5-dioxopyrrolidin-1-yl carbonate (8.5 mg, 0.034 mmol) according to General Procedure H to give 5 mg (20% yield) of the title compound as a pink solid. Anal. Calcd. for C28H34N4O3 m/z 474.5, found: 475.3 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.90 (d, J=8.8 Hz, 2H), 7.71 (s, 1H), 7.39 (s, 1H), 7.24-7.08 (m, 5H), 6.98 (d, J=8.7 Hz, 2H), 4.79 (s, 2H), 3.67-3.53 (m, 1H), 3.53-3.42 (m, 2H), 3.42-3.30 (m, 2H), 3.29-3.19 (m, 2H), 2.22 (d, J=10.4 Hz, 1H), 2.14-1.85 (m, 5H), 1.84-1.54 (m, 4H), 1.44-1.19 (m, 2H).
Workup
- customBenzyl (1R,2R)-2-((S)-1-(4-(oxazol-2-yl)phenyl)piperidin-3-ylamino)cyclohexylcarbamate was synthesized
Sources & evidence
- ORD record
- ord-9aa9f39e624845e7afa38cb02886912a
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710049B2
Reaction notes
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