Tetrahydrofuran → N-(4-Naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-5-yl)-oxalamic acid

Participants

Reaction Steps

To a suspension of N-(4-Naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-5-yl)-oxalamic acid methyl ester, I-61 (95 mg,) in methanol (2.0 mL), 1.0 M NaOH (0.5 mL) was added followed by THF (2.0 mL) resulting in a clear solution. Reaction was stirred at room temperature for 30 minutes and then concentrated to remove the solvents. The residue was taken in water (2.0 mL), acidified with 1.0 M HCl and extracted with EtOAc (5.0 mL×4). Combined extracts were washed with water (5.0 mL), dried (brine, Na2SO4) and concentrated to afford N-(4-Naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-5-yl)-oxalamic acid, I-62 (69 mg). APCI m/z 375 (M-H)+.

Provenance & Evidence