Benzyl 4-oxopiperidine-1-carboxylate → Benzyl 4-{(3R)-3-[(([3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-1-yl}piperidine-1-carboxylate
Reaction equation
COC1N=CC([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:19][CH2:18][C@@H:17]([NH:20][C:21](=[O:36])[CH2:22][NH:23][C:24](=[O:35])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=4)[CH2:16]3)[CH2:11][CH2:10]2)=CC=1.O=C1CCN([C:44]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:45])CC1.COC1N=CC(N2CCC(=O)CC2)=CC=1>>[F:34][C:31]([F:32])([F:33])[C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[C:24]([NH:23][CH2:22][C:21]([NH:20][C@@H:17]1[CH2:18][CH2:19][N:15]([CH:12]2[CH2:11][CH2:10][N:9]([C:44]([O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[O:45])[CH2:14][CH2:13]2)[CH2:16]1)=[O:36])=[O:35]Participants
4
Reactant 3
Product 1
Procedure
The title compound was synthesized in similar fashion to N-[2-({(3R)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide, whereby benzyl 4-oxopiperidine-1-carboxylate was substituted for 1-(6-methoxypyridin-3-yl)piperidin-4-one, and was isolated as a white solid. 1H-NMR (CD3OD) δ: 1.30-1.45 (m, 2H), 1.64-1.18 (m, 1H), 1.84-2.00 (m, 2H), 2.08-2.38 (m, 2H), 2.50-2.64 (m, 2H), 2.80-3.00 (m, 4H), 3.20-3.40 (m, 2H), 4.03 (s, 2H), 4.08-4.13 (m, 2H), 4.34-4.44 (m, 1H), 5.12 (s, 2H), 7.35 (m, 5H), 7.70 (t, J=7.8 Hz, 1H), 7.86 (d, J=7.8 Hz, 1H), 8.14 (d, J=7.5 Hz, 1H), 8.22 (s, 1H). MS m/z: 533 (M+1).
Workup
- customwas isolated as a white solid
Sources & evidence
- ORD record
- ord-d32685a55165436dbed469ffd0ade98f
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067457B2
Reaction notes
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