(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one → HCID 70652102, compound

HRID 1528647Notes

Reaction equation

[OH:1][C:2]([CH3:35])([CH3:34])[CH2:3][C@@:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16](B3OC(C)(C)C(C)(C)O3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.Br[C:37]1[CH:38]=[N:39][C:40]([N:43]2[CH2:46][C:45]([F:48])([F:47])[CH2:44]2)=[N:41][CH:42]=1>>[F:48][C:45]1([F:47])[CH2:46][N:43]([C:40]2[N:39]=[CH:38][C:37]([C:16]3[CH:15]=[CH:14][C:13]([C@@H:11]([N:7]4[CH2:6][CH2:5][C@:4]([CH2:3][C:2]([OH:1])([CH3:34])[CH3:35])([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[O:9][C:8]4=[O:10])[CH3:12])=[CH:18][CH:17]=3)=[CH:42][N:41]=2)[CH2:44]1

Participants

Reactant 2

HCID 59532385(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

HCID 67997452HCID 67997452, compound

Product 1

HCID 70652102HCID 70652102, compound

Procedure

The title compound was prepared following a procedure analogous to Example 31 using (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-{(S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl}-1,3-oxazinan-2-one and 5-bromo-2-(3,3-difluoroazetidin-1-yl)pyrimidine. LC (method 5): tR=1.7 min; Mass spectrum (ESI+): m/z=523 [M+H]+; 1H NMR (CD3OD) δ 0.94 (s, 3H), 1.25 (s, 3H), 1.54 (d, 3H), 2.14 (s, 2H), 2.20 (m, 1H), 2.46 (m, 2H), 3.03 (m, 1H), 4.51 (m, 4H), 5.57 (q, 1H), 7.07 (d, 2H), 7.25-7.40 (m, 7H), 8.60 (s, 2H).

Sources & evidence

ORD record: ord-e2245e3fd59343788d0b23c1d74db060
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090605B2

Reaction notes

Loading…