2-Methylpyridine-4-boronic acid → (R)-3-((S)-1-(4-(2-methylpyridin-4-yl)phenyl)ethyl)-6-phenyl-6-(2-(1,1-dioxoisothiazolidin-2-yl)ethyl)-1,3-oxazinan-2-one

HRID 2037704Notes

Reaction equation

HRID 2037704 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:22][CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][S:25]3(=[O:30])=[O:29])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:12][C:11]2=[O:31])[CH3:9])=[CH:4][CH:3]=1.[CH3:32][C:33]1[CH:38]=[C:37](B(O)O)[CH:36]=[CH:35][N:34]=1>>[CH3:32][C:33]1[CH:38]=[C:37]([C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]3[CH2:15][CH2:14][C@:13]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)([CH2:22][CH2:23][N:24]4[CH2:28][CH2:27][CH2:26][S:25]4(=[O:30])=[O:29])[O:12][C:11]3=[O:31])[CH3:9])=[CH:4][CH:3]=2)[CH:36]=[CH:35][N:34]=1

Participants

3

Reactant 2

HCID 41926642-Methylpyridine-4-boronic acidHCID 59635736(S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-(1,1-dioxo-isothiazolidin-2-yl)ethyl)-6-phenyl-1,3-oxazinan-2-one

Product 1

HCID 66857254(R)-3-((S)-1-(4-(2-methylpyridin-4-yl)phenyl)ethyl)-6-phenyl-6-(2-(1,1-dioxoisothiazolidin-2-yl)ethyl)-1,3-oxazinan-2-one

Procedure

The title compound was prepared from (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-(1,1-dioxo-isothiazolidin-2-yl)ethyl)-6-phenyl-1,3-oxazinan-2-one and 2-methylpyridine-4-boronic acid following a procedure analogous to that described in Example 459 Step 1.

Sources & evidence

ORD record
ord-d2cb01d1f55d45a191cb2f370d1603fc
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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