4-Iodo-1,2-dihydropyridin-2-one → (S)-6-(2-hydroxy-2-methylpropyl)-3-((S)-1-(4-((2-oxo-1,2-dihydropyridin-4-yl)ethynyl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one

HRID 333908

Reaction equation

HRID 333908 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([N:11]2[CH2:16][CH2:15][C@:14]([CH2:23][C:24]([OH:27])([CH3:26])[CH3:25])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:13][C:12]2=[O:28])[CH3:10])=[CH:5][CH:4]=1)#[CH:2].I[C:30]1[CH:35]=[CH:34][NH:33][C:32](=[O:36])[CH:31]=1>>[OH:27][C:24]([CH3:25])([CH3:26])[CH2:23][C@@:14]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[O:13][C:12](=[O:28])[N:11]([C@H:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[C:2][C:30]3[CH:35]=[CH:34][NH:33][C:32](=[O:36])[CH:31]=3)=[CH:8][CH:7]=2)[CH3:10])[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 205825354-Iodo-1,2-dihydropyridin-2-oneHCID 86670541(S)-3-((S)-1-(4-ethynylphenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one

Product 1

HCID 49870703(S)-6-(2-hydroxy-2-methylpropyl)-3-((S)-1-(4-((2-oxo-1,2-dihydropyridin-4-yl)ethynyl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one

Procedure

The title compound was prepared from (S)-3-((S)-1-(4-ethynylphenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one and 4-iodopyridin-2(1H)-one following a procedure analogous to that described in Example 28 Step 3. LC-MS Method 1 tR=1.3 min, m/z=471 (M+1). 1H NMR (CD3OD) 7.44-7.28 (m, 8H), 6.97 (d, 2H), 6.64 (s, 1H), 6.44 (dd, 1H), 5.54 (q, 1H), 3.02 (dt, 1H), 2.49 (m, 2H), 2.21 (m, 1H), 2.15 (s, 2H), 1.53 (d, 3H), 1.26 (s, 3H), 0.96 (s, 3H).

Sources & evidence

ORD record
ord-925063b9e2c44bb9b9724c4ec0d866fd
Source dataset
uspto-grants-2014_11
Patent number
US08883778B2

Linked notes

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