(S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one → (S)-3-((S)-1-(4-(6-(cyclopentyloxy)pyridin-2-yl)phenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one
Reaktionsgleichung
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1.[CH:28]1([O:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36](B3OC(C)(C)C(C)(C)O3)[N:35]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1>>[CH:28]1([O:33][C:34]2[N:35]=[C:36]([C:2]3[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]4[CH2:15][CH2:14][C@:13]([CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])([C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)[O:12][C:11]4=[O:27])[CH3:9])=[CH:6][CH:7]=3)[CH:37]=[CH:38][CH:39]=2)[CH2:29][CH2:30][CH2:31][CH2:32]1Komponenten
3
Edukt 2
Produkt 1
Versuchsvorschrift
The title compound was prepared from (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one and 2-(cyclopentyloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine following a procedure analogous to that described in Example 14. LC-MS Method 1 tR=2.23 min, m/z=515, 457; 1H NMR (CD3OD) 0.96 (s, 3H), 1.27 (s, 3H), 1.56 (d, 3H), 1.70 (2H), 1.85 (4H), 2.05 (2H), 2.17 (s, 2H), 2.24 (m, 1H), 2.46 (2H), 3.05 (m, 1H), 5.47 (m, 1H), 5.58 (q, 1H), 6.70 (d, 1H), 7.00 (d, 2H), 7.25-7.40 (6H), 7.70 (t, 1H), 7.77 (d, 2H).