Hydrogen Peroxide → HCID 58109674, compound

HRID 1046205Notes

Reaction equation

HRID 1046205 reaction equation
[OH:1][C:2]([CH3:34])([CH3:33])[CH2:3][C@@:4]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][N:20]=3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.OO.C([O-])([O-])=[O:38].[K+].[K+]>CS(C)=O>[OH:1][C:2]([CH3:33])([CH3:34])[CH2:3][C@@:4]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:26]=[CH:25][C:22]([C:23]([NH2:24])=[O:38])=[CH:21][N:20]=3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 58109371HCID 58109371, compound

Product 1

HCID 58109674HCID 58109674, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6-(4-((S)-1-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)nicotinonitrile (120 mg, 0.26 mmol) in DMSO (8 mL) were added H2O2 (0.5 mL, 30%) and K2CO3 (35 mg, 0.26 mmol), and the mixture was stirred at rt for 3 h. The reaction was quenched with H2O (10 mL) and the mixture was extracted with EtOAc (4×20 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated to give the crude product, which was purified by preparative HPLC to give 6-(4-((S)-1-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)nicotinamide (55.46 mg, 45%). LC-MS Method 2 tR=1.12 min, m/z=474, 416. 1H NMR (CDCl3): 1.03 (s, 3H), 1.09 (s, 3H), 1.46 (d, 3H), 2.13-2.26 (m, 5H), 2.30 (m, 1H), 2.44 (s, 1H), 2.79 (d, 1H), 5.61 (m, 1H), 6.15-6.38 (s, 1H), 6.97 (d, 2H), 7.13-7.29 (m, 5H), 7.60 (d, 2H), 7.70 (d, 2H), 8.15 (d, 1H), 9.05 (s, 1H).

Workup

  1. customThe reaction was quenched with H2O (10 mL)
  2. extractionthe mixture was extracted with EtOAc (4×20 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-f2bfaadd4a084e7b879f1d036dc358d8
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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