(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide → Ethyl3-[(4-{4-[((2R)-2-hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl}-ethyl)amino]-1-piperidinyl}benzoyl)amino]propanoate
Reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][NH:7][C:8](=[O:22])[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[CH3:2].[NH2:24][CH2:25][C@@H:26]([C:28]1[CH:29]=[CH:30][C:31]([OH:39])=[C:32]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH:33]=1)[OH:27]>>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][NH:7][C:8](=[O:22])[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][CH:18]([NH:24][CH2:25][C@H:26]([OH:27])[C:28]3[CH:29]=[CH:30][C:31]([OH:39])=[C:32]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH:33]=3)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[CH3:2]Participants
Reactant 2
Product 1
Procedure
The title compound was prepared from 3-[4-(4-oxo-piperidine-1-yl)-benzoylamino]-propionic acid ethyl ester (which was obtained in Example 158) 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 179 as a white solid; mp >95° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.17 (t, J=7.1 Hz, 3H), 1.40-1.60 (m, 2H), 1.90-2.10 (m, 2H), 2.54 (t, J=7.0 Hz, 2H), 2.70-2.95 (m, 5H), 2.94 (s, 3H), 3.35-3.50 (m, 2H), 3.80-3.95 (m, 2H), 4.05 (q, J=7.1 Hz, 2H), 4.65-4.75 (m, 1H), 6.88 (d, J=8.2 Hz, 1H), 6.95 (d, J=8.9 Hz, 2H), 7.05 (dd, J=8.2, 1.9 Hz, 1H), 7.22 (d, J=1.9 Hz, 1H), 7.69 (d, J=8.9 Hz, 2H), 8.26 (t, J=5.2 Hz, 1H); MS (ES) m/z: 549.2 (MH+); HRMS Calcd. for C26H37N4O7S(MH+): 549.2377. Found: 549.2369.
Sources & evidence
- ORD record
- ord-d4de6d9734634bdeab9ae846082f1d34
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06525202B2
Reaction notes
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