Tetrahydrofuran → HCID 86754235, compound

Participants

Reaction Conditions

Reaction Steps

To a flame dried flask under an inert atmosphere containing 8-[[(phenylmethoxy)carbonyl]amino]-pyrazino[2, 1-c] [1, 4]benzoxazine-3(4 H)-carboxylic acid phenylmethyl ester (Step 7, 1.00 g, 2.11 mmol) in tetrahydrofuran (20 mL) cooled to -78° C. is added n-butyl lithium (1.6 M in hexanes) (1.39 mL, 2.22 mmol) followed by (R)-glycidyl butyrate (0.33 mL, 2.32 mmol). The reaction is stirred 15 hours and quenched with saturated ammonium chloride (20 mL). The aqueous phase is separated and extracted with ethyl acetate (2×20 mL). The organics are combined, washed with saline, dried over Na2SO4, concentrated in vacuo, and chromatographed on silica gel (230-400 mesh, 200 mL), eluting with chloroform/methanol (99/1). The appropriate fractions are combined (Rf =0.16, TLC, chloroform/methanol, 95/5) and concentrated in vacuo to give the title compound, NMR (CDCl3) 7.39-7.31, 7.04, 6.96, 6.75, 5.16, 4.68, 4.20-3.99, 4.15, 3.96-3.86, 3.73-3.62, 3.16-2.97, 2.82-2.66.

Provenance & Evidence