Hydrogen Peroxide → HCID 58109357, compound

HRID 1046202Notes

Reaction equation

HRID 1046202 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C@@:5]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:10][C:9](=[O:11])[N:8]([C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][N:21]=3)=[CH:16][CH:15]=2)[CH3:13])[CH2:7][CH2:6]1.OO.C([O-])([O-])=[O:37].[K+].[K+].O>CS(C)=O.CCOC(C)=O>[OH:1][CH2:2][CH2:3][CH2:4][C@@:5]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:10][C:9](=[O:11])[N:8]([C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:27]=[CH:26][C:23]([C:24]([NH2:25])=[O:37])=[CH:22][N:21]=3)=[CH:16][CH:15]=2)[CH3:13])[CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 58109388HCID 58109388, compound

Product 1

HCID 58109357HCID 58109357, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-(4-((S)-1-((R)-6-(3-hydroxypropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)nicotinonitrile (50 mg, 0.11 mmol) and H2O2 (0.04 mL, 30%), K2CO3 (6.27 mg, 0.046 mmol) in DMSO (0.39 mL) was stirred overnight at room temperature. The reaction was added water and EtOAc. The layer was separated. The organic phase was washed with brine and dried, concentrated to give the product (9.95 mg, 19%) LC-MS Method 2 tR=1.083, m/z=460.1; 1H NMR (CD3OD) 1.21 (m, 1H), 1.51 (d, 3H), 1.53-1.64 (m, 1H), 1.85-1.94 (m, 2H), 2.10-2.21 (m, 1H), 2.29 (m, 1H), 2.42 (m, 1H), 3.03 (m, 1H), 3.39 (t, 2H), 5.52 (m, 1H), 6.99 (d, 2H), 7.21-7.34 (m, 5H), 7.22 (d, 2H), 7.31 (d, 1H), 8.22 (d, 1H), 8.98 (s, 1H).

Workup

  1. customThe layer was separated
  2. washThe organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e0405e93a09843dd805a8b9c7564dcaf
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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