Methanol → (R)-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylic acid

HRID 1501206Notes

Reaction equation

[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[CH:4][N:3]1[C@@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13].O.[OH-].[Li+].O.CO>O1CCCC1>[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][N:3]1[C@@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13]

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of (R)-methyl 2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylate (451 mg, 1.75 mmol), lithium hydroxide monohydrate (369 mg, 8.77 mmol), water (4 mL) and methanol (4 mL) in tetrahydrofuran (12 mL) was stirred at 20° C. for 12 hours. The reaction mixture was concentrated. The residue was acidified with concentrated hydrochloride solution to pH=2. The mixture was extracted with ethyl acetate (20 mL×2). The organic phase was dried over sodium sulfate and filtered. The filtrate was concentrated. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:2) to give (R)-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylic acid as a white solid (336 mg, 80%). LRMS (M+H+) m/z: calcd 243.13. found 243.

Workup

concentrationThe reaction mixture was concentrated
extractionThe mixture was extracted with ethyl acetate (20 mL×2)
dry with materialThe organic phase was dried over sodium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated
customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:2)

Sources & evidence

ORD record: ord-3d6f95ffdd4345649371b01fb030891b
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206128B2

Reaction notes

Loading…