(S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one → HCID 54771526, compound

HRID 1426045Notes

Reaction equation

HRID 1426045 reaction equation
CC1(C)C(C)(C)OB([C:9]2[N:14]=[C:13]([N:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]3=[O:21])[CH:12]=[CH:11][CH:10]=2)O1.Br[C:24]1[CH:29]=[CH:28][C:27]([C@@H:30]([N:32]2[CH2:37][CH2:36][C@:35]([CH2:44][C:45]([OH:48])([CH3:47])[CH3:46])([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[O:34][C:33]2=[O:49])[CH3:31])=[CH:26][CH:25]=1>>[OH:48][C:45]([CH3:46])([CH3:47])[CH2:44][C@@:35]1([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:34][C:33](=[O:49])[N:32]([C@H:30]([C:27]2[CH:26]=[CH:25][C:24]([C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([N:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]4=[O:21])[N:14]=3)=[CH:29][CH:28]=2)[CH3:31])[CH2:37][CH2:36]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 45785901HCID 45785901, compound

Product 1

HCID 54771526HCID 54771526, compound

Procedure

The title compound was prepared from 1-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]pyridin-2(1H)-one (purchased from CombiPhos Catalysts Inc., Princeton, N.J., USA) and (S)-3-[(S)-1-(4-bromophenyl)ethyl]-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one following a procedure analogous to that described in Example 35. LC (method 5): tR=1.53 min; Mass spectrum (ESI+): m/z=466, 524 [M+H]+; 1H NMR (CD3OD) δ 0.94 (s, 3H), 1.26 (s, 3H), 1.57 (d, 3H), 2.16 (s, 2H), 2.25 (m, 1H), 2.47 (m, 2H), 3.04 (m, 1H), 5.59 (q, 1H), 6.54 (t, 1H), 6.64 (d, 1H), 7.08 (d, 2H), 7.25-7.40 (5H), 7.63 (m, 1H), 7.66 (m, 1H), 7.85-8.00 (5H).

Sources & evidence

ORD record
ord-3b62baaace5f41aab4c3c723334223e8
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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