L-Leucine, ethyl ester, hydrochloride (1:1) → 4-Methyl-(2S)-2-[4-(4-oxo-piperidin-1-yl)-benzoylamino]-pentanoic acid ethyl ester
Reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.Cl.[CH2:18]([O:20][C:21](=[O:28])[C@H:22]([CH2:24][CH:25]([CH3:27])[CH3:26])[NH2:23])[CH3:19]>>[CH2:18]([O:20][C:21](=[O:28])[C@@H:22]([NH:23][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([N:5]2[CH2:4][CH2:3][C:2](=[O:1])[CH2:7][CH2:6]2)=[CH:16][CH:15]=1)[CH2:24][CH:25]([CH3:26])[CH3:27])[CH3:19]Participants
3
Procedure
The title compound was prepared from 4-(4-oxo-piperidine-1-yl)-benzoic acid (which was obtained in Example 151) and L-leucine ethyl ester hydrochloride according to the procedure of Example 154 as a white flake; 1H NMR (300 MHz, CDCl3) δ 0.99 (t, J=6.2 Hz, 6H), 1.30 (t, J=7.1 Hz, 3H), 1.60-1.80 (m, 3H), 2.56 (t, J=6.0 Hz, 4H), 3.72 (t, J=6.0 Hz, 4H), 4.22 (q, J=7.1 Hz, 2H), 4.80-4.90 (m, 1H), 6.42 (d, J=8.2 Hz, 1H), 6.94 (d, J=7.0 Hz, 2H), 7.77 (d, J=7.0 Hz, 1H); MS (ES) m/z: 361.3 (MH+); HRMS Calcd. for C20H28N20O4 (M+): 360.2049. Found: 360.2081.
Sources & evidence
- ORD record
- ord-7522ae5309e947b3a40a4505e5814d9c
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06525202B2
Reaction notes
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