1-[5-(2-Ethoxy-2-oxoethoxy)-6-nitropyridin-2-yl]-5-oxopyrrolidin-3-carboxylic acid methyl ester → 5-Oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-carboxylic acid methyl ester

HRID 1847007Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19](OCC)=[O:20])=[C:13]([N+:24]([O-])=O)[N:12]=2)[CH2:6]1)=[O:4]>C(O)(=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]3[O:17][CH2:18][C:19](=[O:20])[NH:24][C:13]=3[N:12]=2)[CH2:6]1)=[O:4]

Participants

Conditions

Temperature: 85 °C

Procedure

Reduced iron (55.7 mg, 0.996 mmol) was added to a solution of 1-[5-(2-ethoxy-2-oxoethoxy)-6-nitropyridin-2-yl]-5-oxopyrrolidin-3-carboxylic acid methyl ester (122 mg, 0.332 mmol) in acetic acid (1.2 ml) and the mixture was stirred at 85° C. for 2 hours. After cooling, the insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in dichloromethane, a saturated sodium hydrogen carbonate aqueous solution was added thereto and the mixture was stirred for 10 minutes. The organic layer was separated, dried over anhydrous magnesium sulfate and then the solvent was removed under reduced pressure to yield 81 mg (84%) of the title compound in the form of a colorless solid.

Workup

temperatureAfter cooling
customthe insoluble material was removed by filtration
concentrationthe filtrate was concentrated under reduced pressure
dissolutionThe residue was dissolved in dichloromethane
additiona saturated sodium hydrogen carbonate aqueous solution was added
stirringthe mixture was stirred for 10 minutes
customThe organic layer was separated
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-52087f489c5646dc83d90c40f9ed0711
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952010B2

Reaction notes

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