(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 → (S)-6-(2-Hydroxy-2-methyl-propyl)-3-((S)-1-{4-[6-(1-methyl-2-oxo-pyrrolidin-3-yl)-pyridin-3-yl]-phenyl}-ethyl)-6-phenyl-[1,3]oxazinan-2-one

HRID 1528665Notes

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]=[CH:39][C:40]([CH:43]2[CH2:47][CH2:46][N:45]([CH3:48])[C:44]2=[O:49])=[N:41][CH:42]=1>>[OH:1][C:2]([CH3:35])([CH3:34])[CH2:3][C@@:4]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:14]=[CH:15][C:16]([C:37]3[CH:42]=[N:41][C:40]([CH:43]4[CH2:47][CH2:46][N:45]([CH3:48])[C:44]4=[O:49])=[CH:39][CH:38]=3)=[CH:17][CH:18]=2)[CH3:12])[CH2:6][CH2:5]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 679978423-(5-Bromo-pyridin-2-yl)-1-methyl-pyrrolidin-2-one

Product 1

HCID 70652109(S)-6-(2-Hydroxy-2-methyl-propyl)-3-((S)-1-{4-[6-(1-methyl-2-oxo-pyrrolidin-3-yl)-pyridin-3-yl]-phenyl}-ethyl)-6-phenyl-[1,3]oxazinan-2-oneYield 57%

Procedure

The title compound was prepared from (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 3-(5-bromo-pyridin-2-yl)-1-methyl-pyrrolidin-2-one following a procedure analogous to that described in Example 1. Yield: 57% of theory; LC (method 1): tR=1.82 min; Mass spectrum (ESI+): m/z=528 [M+H]+.

Sources & evidence

ORD record: ord-b826d518647e4945bbeace881aadb901
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090605B2

Reaction notes

Loading…