Ethyl {[4-(4-oxo-1-piperidinyl)benzoyl]amino}acetate → Ethyl[(4-{4-[((2R)-2-hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidinyl}benzoyl)amino]acetate
Reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:22]=[CH:21][C:11]([C:12]([NH:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:23][CH2:24][C@@H:25]([C:27]1[CH:28]=[CH:29][C:30]([OH:38])=[C:31]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:32]=1)[OH:26]>>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][NH:14][C:12](=[O:13])[C:11]1[CH:21]=[CH:22][C:8]([N:5]2[CH2:6][CH2:7][CH:2]([NH:23][CH2:24][C@H:25]([OH:26])[C:27]3[CH:28]=[CH:29][C:30]([OH:38])=[C:31]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:32]=3)[CH2:3][CH2:4]2)=[CH:9][CH:10]=1)[CH3:20]Participants
Reactant 2
Product 1
Procedure
The title compound was prepared from ethyl {[4-(4-oxo-1-piperidineyl)benzoyl]amino}acetate (which was obtained in Example 161) 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 a white solid; mp >140° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.20 (t, J=7.1 Hz, 3H), 1.20-1.35 (m, 2H), 1.75-1.90 (m, 2H), 2.50-2.90 (m, 5 H), 2.90 (s, 3H), 3.70-3.85 (m, 2H), 3.93 (d, J=5.8 Hz, 2H), 4.10 (q, J=7.1 Hz, 2H), 4.47 (dd, J=7.9, 4.4 Hz, 1H), 6.79 (d, J=8.3 Hz, 1H), 6.90-7.00 (m, 3H), 7.16 (d, J=2.0 Hz, 1H), 7.72 (d, J=8.9 Hz, 2H), 8.58 (t, J=5.8 Hz, 1H); MS (ES) m/z: 535.2 (MH+); HRMS Calcd. for C26H37N4O7S(MH+): 535.2221. Found: 535.2216.
Sources & evidence
- ORD record
- ord-1121fe1e6c944b11b2a4f073c0c5aa90
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06525202B2
Reaction notes
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