Hydrogen Peroxide → HCID 58109588, compound

HRID 884369Notes

Reaction equation

HRID 884369 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([CH2:29][CH2:30][CH2:31][OH:32])[O:13][C:12](=[O:14])[N:11]([C@H:15]3[CH2:20][CH2:19][CH2:18][N:17]([C:21]4[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=4)[CH2:16]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.OO.C([O-])([O-])=[O:36].[K+].[K+].O>CS(C)=O.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([CH2:29][CH2:30][CH2:31][OH:32])[O:13][C:12](=[O:14])[N:11]([C@H:15]3[CH2:20][CH2:19][CH2:18][N:17]([C:21]4[CH:28]=[CH:27][C:24]([C:25]([NH2:26])=[O:36])=[CH:23][N:22]=4)[CH2:16]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 58109452HCID 58109452, compound

Product 1

HCID 58109588HCID 58109588, compoundYield 159.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-((S)-3-((R)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-2-oxo-1,3-oxazinan-3-yl)piperidin-1-yl)nicotinonitrile (520 mg, 1.19 mmol) in DMSO (10 mL) was added H2O2 (30%, 1 mL) and K2CO3 (82 mg, 0.59 mmol). The mixture was stirred at rt for 1 d. After water and EtOAc were added, the mixture was extracted with EtOAc. The organic layers were dried and concentrated to give 6-((S)-3-((R)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-2-oxo-1,3-oxazinan-3-yl)piperidin-1-yl)nicotinamide (430 mg, 79%). LC-MS Method 2 tR=0.99 min, m/z=457. 1H NMR (400 MHz, CDCl3): 1.29-1.30 (m, 1H), 1.58-1.63 (m, 2H), 1.82-1.86 (m, 2H), 1.91-2.00 (m, 3H), 2.21-2.32 (m, 1H), 2.49-2.52 (m, 1H), 2.65-2.71 (m, 1H), 2.81-2.96 (m, 3H), 3.39 (m, 1H), 3.42-4.48 (m, 2H), 3.87(m, 1H), 4.21-4.24 (m, 1H), 4.30 (s, 1H), 6.75-6.78 (d, 1H), 7.39-7.72 (t, 2H), 7.94-7.97 (m,1H), 8.59-8.60 (s, 1H).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. customThe organic layers were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-262206d226354417ab47e83539fb0947
Source dataset
uspto-grants-2012_08
Patent number
US08242111B2

Reaction notes

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