(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-[5-(1-methanesulfonyl-cyclopropyl)-pyridin-2-yl]-phenyl}-ethyl)-6-phenyl-[1,3]oxazinan-2-one

HRID 1426030Notes

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.Cl[C:37]1[CH:42]=[CH:41][C:40]([C:43]2([S:46]([CH3:49])(=[O:48])=[O:47])[CH2:45][CH2:44]2)=[CH:39][N:38]=1>>[OH:1][C:2]([CH3:34])([CH3:35])[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:18]=[CH:17][C:16]([C:37]3[CH:42]=[CH:41][C:40]([C:43]4([S:46]([CH3:49])(=[O:47])=[O:48])[CH2:45][CH2:44]4)=[CH:39][N:38]=3)=[CH:15][CH:14]=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 866961442-Chloro-5-(1-methanesulfonylcyclopropyl)pyridine

Product 1

HCID 70651290(S)-6-(2-Hydroxy-2-methyl-propyl)-3-((S)-1-{4-[5-(1-methanesulfonyl-cyclopropyl)-pyridin-2-yl]-phenyl}-ethyl)-6-phenyl-[1,3]oxazinan-2-oneYield 20%

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 2-chloro-5-(1-methanesulfonyl-cyclopropyl)-pyridine following a procedure analogous to that described in Example 1. Yield: 20% of theory; LC (method 1): tR=1.83 min; Mass spectrum (ESI+): m/z=549 [M+H]+.

Sources & evidence

ORD record: ord-a2c8f26fa9b0441189c482ad20900b96
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933072B2

Reaction notes

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