Ethanol → HCID 14501375, compound

Participants

Reaction Conditions

Reaction Steps

A slurry of 701 g of ethyl (S)-10-azido-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate in 6.0 of dimethylformamide was charged to the five gallon autoclave. After placing the vessel under nitrogen, a slurry of 45 g of 10% palladium-on-carbon in 700 ml of dimethylformamide was added. The mixture was hydrogenated at 48-50 psi and 600 RPM. A 10° C. rise in temperature was observed during the first thirty minutes of reaction. The reaction mixture was filtered and washed with 2×3 L of dimethylformamide. Concentration of the filtrate under aspirator pressure gave a very thick, dark residue (volume~700 ml). Ethanol (1.2 L) was added and the suspension was refluxed briefly. After cooling to 0° C., the product was collected, washed with 3×300 ml of cold ethanol and dried for eighteen hours at 80° C. in vacuo to give 508 g of product which was shown to be 97.6% pure by HPLC.

Provenance & Evidence