Sodium Bicarbonate → 5-ethyl 6-tert-butyl 2-methoxy-7,8-dihydro-1,6-naphthyridine-5,6(5H)-dicarboxylate

HRID 2202236Notes

Reaction equation

F[B-](F)(F)F.[CH3:6][O+](C)C.[OH:10][C:11]1[CH:20]=[CH:19][C:18]2[CH:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:16]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:15][CH2:14][C:13]=2[N:12]=1.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:6][O:10][C:11]1[CH:20]=[CH:19][C:18]2[CH:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:16]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:15][CH2:14][C:13]=2[N:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Trimethyloxonium tetrafluoroborate (1.775 g, 12.00 mmol) was added to a mixture of 5-ethyl 6-tert-butyl 2-hydroxy-7,8-dihydro-1,6-naphthyridine-5,6(5H)-dicarboxylate (1.289 g, 4.00 mmol) and acetonitrile (18 mL) at 0° C. The mixture was stirred at 0° C. for 2 hr, and the reaction mixture was poured into ice-cooled saturated aqueous sodium hydrogencarbonate solution (100 mL), and the mixture was extracted with ethyl acetate (×3). The organic layer was washed with water and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 2→19% ethyl acetate/hexane) to give 5-ethyl 6-tert-butyl 2-methoxy-7,8-dihydro-1,6-naphthyridine-5,6(5H)-dicarboxylate (372 mg, 1.106 mmol, 28%) as a colorless oil.

Workup

additionthe reaction mixture was poured into ice-
extractionthe mixture was extracted with ethyl acetate (×3)
washThe organic layer was washed with water and brine
dry with materialdried over magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 2→19% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-0eb3b9c2a61940138c76fbb63b9d892b
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365520B2

Reaction notes

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