3-Cyclohexyl-L-alanine → (2S)-2-[(5-chloro-1,3-benzoxazol-2-yl)amino]-3-cyclohexyl-N-{2-[(4-fluorophenyl)amino]ethyl}propanamide
Reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:5]=2[N:6]=1.[CH2:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C@H:19]([NH2:23])[C:20]([OH:22])=O)[CH2:14][CH2:13]1.Cl.Cl.[F:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][CH2:34][CH2:35][NH2:36])=[CH:29][CH:28]=1>>[Cl:11][C:8]1[CH:9]=[CH:10][C:4]2[O:3][C:2]([NH:23][C@@H:19]([CH2:18][CH:15]3[CH2:14][CH2:13][CH2:12][CH2:17][CH2:16]3)[C:20]([NH:36][CH2:35][CH2:34][NH:33][C:30]3[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=3)=[O:22])=[N:6][C:5]=2[CH:7]=1Participants
4
Procedure
The title compound was prepared from 2,5-dichlorobenzooxazole, L-cyclohexylalanine and N1-(4-fluoro-phenyl)-ethane-1,2-diamine-2HCl using the procedure analogous to that described in example 2. 1H NMR (DMSO-d6, 400 MHz) a 8.35 (d, 1H, J=8 Hz), 8.18 (t, 1H, J=5.8 Hz), 7.30 (d, 1H, J=8.4 Hz), 7.18 (d, 1H, J=2.0 Hz), 6.90 (dd, 1H, J=8.4 Hz, J=2.0 Hz), 6.84(m, 2H), 6.51(m, 2H), 4.19(m, 1H), 3.15(m, 2H), 2.98(m, 2H), 1.55(m, 7H), 1.30(m, 1H), 1.05(m, 3H), 0.83(m, 2H). HPLC-MS calcd. for C24H28ClFN4O2(M+H+) 459.19. found 459.4.
Sources & evidence
- ORD record
- ord-6321afd6a0a24d4e81f8abd51e6f5b15
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07173051B2
Reaction notes
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