4-Methyl-(2S)-2-[4-(4-oxo-piperidin-1-yl)-benzoylamino]-pentanoic acid ethyl ester → HCID 10793544, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C@@H:5]([NH:10][C:11](=[O:25])[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].[NH2:27][CH2:28][C@@H:29]([C:31]1[CH:32]=[CH:33][C:34]([OH:42])=[C:35]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:36]=1)[OH:30]>>[CH2:1]([O:3][C:4](=[O:26])[C@@H:5]([NH:10][C:11](=[O:25])[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:19][CH2:20][CH:21]([NH:27][CH2:28][C@H:29]([OH:30])[C:31]3[CH:32]=[CH:33][C:34]([OH:42])=[C:35]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:36]=3)[CH2:22][CH2:23]2)=[CH:14][CH:13]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]Participants
Procedure
The title compound was prepared from ethyl 4-methyl-2-[(2S)-4-(4-oxo-piperidin-1-yl)-benzoylamino]-pentanoic acid ethyl ester (which was obtained in Example 165) and N-[5-((1R)-2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 10) according to the procedure of Example 180 as an off-white solid; mp>85° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 0.86 (d, J=6.3 Hz, 3 H), 0.92 (d, J=6.3 Hz, 3 H), 1.18 (t, J=7.1 Hz, 3 H), 1.20–1.40 (m, 2 H), 1.45–1.95 (m, 5 H), 2.55–2.92 (m, 5 H), 2.92 (s, 3 H), 3.70–3.85 (m, 2 H), 4.10 (q, J=7.1 Hz, 2 H), 4.40–4.55 (m, 2 H), 6.82 (d, J=8.3 Hz, 1 H), 6.94 (d, J=8.9 Hz, 2 H), 7.00 (dd, J=8.3, 2.0 Hz, 1 H), 7.18 (d, J=2.0 Hz, 1 H), 7.75 (d, J=8.9 Hz, 2 H), 8.33 (d, J=7.7 Hz, 1 H); MS (ES) m/z: 591.3 (MH+); HRMS Calcd. for C29H43N4O7S (MH+): 591.2847. Found: 591.2840.
Sources & evidence
- ORD record
- ord-3e0ea93cf616449fbdc8e54210fc6e71
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07022716B2
Reaction notes
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