(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

HRID 1046095Notes

Reaction equation

HRID 1046095 reaction equation
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]1

Participants

3

Reactant 2

HCID 44599033(S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-oneHCID 457857732-(Cyclopentyloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Product 1

HCID 58485373(S)-3-((S)-1-(4-(6-(cyclopentyloxy)pyridin-2-yl)phenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one

Procedure

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).

Sources & evidence

ORD record
ord-6731ed9669084d9f8a12f6f6a1b2693c
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

Loading…