Methane → 6-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

HRID 1372902Notes

Reaction equation

[C:1]([C:4]1[C:13]2[O:12][C:11]([CH3:15])([CH3:14])[C:10](=[O:16])[NH:9][C:8]=2[CH:7]=[C:6]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=1)(=[O:3])[CH3:2].[Se](=O)=[O:26].C.[O:29]1CCO[CH2:31][CH2:30]1>O>[CH2:18]([O:17][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH:2]([O:29][CH2:30][CH3:31])[OH:26])[C:13]2[O:12][C:11]([CH3:15])([CH3:14])[C:10](=[O:16])[NH:9][C:8]=2[CH:7]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: -18 °C

Procedure

50.12 g (154 mmol) 8-acetyl-6-benzyloxy-2,2-dimethyl-benzo[1,4]oxazin-3-one are reacted with selenium dioxide as oxidising agent and activated charcoal in refluxing dioxane and some water. After cooling, the solid is filtered off and washed with dioxane. The filtrate is evaporated down and the residue is dissolved in 550 mL ethanol and refluxed for 30 minutes. It is filtered and the mother liquor is cooled to −18° C., during which time a solid is precipitated which is suction filtered. After recrystallisation from ethanol the product is obtained in the form of a beige solid. Yield: 8.95 g (15%).

Workup

temperatureAfter cooling
filtrationthe solid is filtered off
washwashed with dioxane
customThe filtrate is evaporated down
dissolutionthe residue is dissolved in 550 mL ethanol
temperaturerefluxed for 30 minutes
filtrationIt is filtered
customis precipitated which
filtrationfiltered
customAfter recrystallisation from ethanol the product
customis obtained in the form of a beige solid

Sources & evidence

ORD record: ord-29c15422cf4047f4be2ba901555b263e
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07160882B2

Reaction notes

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