(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 54771527, compound

HRID 1426048Notes

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.[CH2:36]([O:38][C:39]([C:41]1([C:44]2[CH:49]=[C:48](Br)[CH:47]=[CH:46][N:45]=2)[CH2:43][CH2:42]1)=[O:40])[CH3:37]>>[CH2:36]([O:38][C:39]([C:41]1([C:44]2[CH:49]=[C:48]([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:47]=[CH:46][N:45]=2)[CH2:43][CH2:42]1)=[O:40])[CH3:37]

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 67997471HCID 67997471, compound

Product 1

HCID 54771527HCID 54771527, compoundYield 81%

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 1-(4-bromo-pyridin-2-yl)-cyclopropanecarboxylic acid ethyl ester following a procedure analogous to that described in Example 1. Yield: 81% of theory; LC (method 3): tR=2.99 min; Mass spectrum (ESI+): m/z=543 [M+H]+.

Sources & evidence

ORD record: ord-d47013c425734afbb2886ac0c7dc8ba9
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933072B2

Reaction notes

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