Hydrogen Peroxide → HCID 66857081, compound

HRID 2037443Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH2:28][CH2:29][OH:30])[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[N:16]=2)[CH2:10][CH2:9]1.[OH:31]O>C(O)(=O)C>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([N:11]3[CH2:10][CH2:9][C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])([CH2:28][CH2:29][OH:30])[O:13][C:12]3=[O:14])[N+:16]=2[O-:31])=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 80 °C

Procedure

6-(2-fluorophenyl)-3-(6-(4-fluorophenyl)pyridin-2-yl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one (680 mg, 1.66 mmol) was added to acetic acid (20 mL), 30% aq hydrogen peroxide (50 mL) was added at rt and the reaction mixture was stirred for about 5 h at 80° C. The mixture was extracted with CH2Cl2 and the organic phase washed with Na2SO3 solution, then dried over Na2SO4. Removal of the solvent gave the crude product, which was purified by HPLC and give 2-(4-fluorophenyl)-6-(6-(2-fluorophenyl)-6-(2-hydroxyethyl)-2-oxo-1,3-oxazinan-3-yl)pyridine 1-oxide (80 mg, 11%). LC-MS Method 2, tR=1.704 min, m/z=427.1. 1H NMR (CD3OD) 2.33-2.50 (m, 2H), 2.60-2.77 (m, 2H), 3.08-3.20 (m, 1H), 3.32-3.40 (m, 1H), 3.40-3.52 (m, 1H), 3.70-3.85 (m, 1H), 7.08-7.37 (m, 5H), 7.40-7.69 (m, 4H), 7.70-7.86 (m, 2H). 1H NMR (400 MHz, CDCl3): δ=2.5 (s, 2H), 2.6 (m, 2H), 3.05 (m, 1H), 3.3 (m, 1H), 3.35-3.6 (m, 1H), 3.75 (m, 1H), 7.0-7.8 (m, 11H).

Workup

additionwas added at rt
extractionThe mixture was extracted with CH2Cl2
washthe organic phase washed with Na2SO3 solution
dry with materialdried over Na2SO4
customRemoval of the solvent
customgave the crude product, which
customwas purified by HPLC

Sources & evidence

ORD record: ord-844857e8bc39433087f2df5cd9ec1ff2
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575156B2

Reaction notes

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