Benzyl 1-(2-(tert-butoxy)-2-oxoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate → 1-(2-(tert-Butoxy)-2-oxoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylic Acid

HRID 2370852Notes

Reaction equation

[C:1]([O:5][C:6](=[O:25])[CH2:7][N:8]1[C:13](=[O:14])[CH:12]=[CH:11][C:10]([C:15]([O:17]CC2C=CC=CC=2)=[O:16])=[CH:9]1)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.CCO.[Pd]>[C:1]([O:5][C:6](=[O:25])[CH2:7][N:8]1[C:13](=[O:14])[CH:12]=[CH:11][C:10]([C:15]([OH:17])=[O:16])=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of benzyl 1-(2-(tert-butoxy)-2-oxoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate (924 mg, 2.69 mmol) in EtOAc (20 mL) and EtOH (5 mL) was treated with palladium 10 wt. % on activated carbon (143 mg, 0.135 mmol) under nitrogen. The reaction vessel was purged through 3 vacuum-hydrogen cycles, and was stirred under a hydrogen balloon at 23° C. After 45 min, the reaction was filtered through Celite® brand filter agent, the filter cake washed with MeOH (100 mL), the filtrates were combined and concentrated, affording the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.02-13.68 (br. s., 1H), 8.49 (br. s., 1H), 7.83 (d, J=9.39 Hz, 1H), 6.44 (d, J=9.19 Hz, 1H), 4.68 (br. s., 2H), 1.41 (s, 9H). MS (ESI, positive ion) m/z: 276.0 (M+H).

Workup

customThe reaction vessel was purged through 3 vacuum-hydrogen cycles
filtrationthe reaction was filtered through Celite® brand
filtrationfilter agent
washthe filter cake washed with MeOH (100 mL)
concentrationconcentrated

Sources & evidence

ORD record: ord-a40219d469644f46969feb1f309e1d67
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710043B2

Reaction notes

Loading…