Ethyl Acetate → (Z)-2-benzyloxycarbonylamino-3-(6-methoxy-[1,5]naphthyridin-4-yl)-acrylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of benzyloxycarbonylamino-(dimethoxy-phosphoryl)-acetic acid methyl ester (2.07 g, 6.25 mmol) in DCM (10 mL) was cooled to 0° C. and DBU (0.95 g, 6.25 mmol) was added dropwise. The mixture was stirred at 0° C. for 15 min and then added via syringe dropwise to a suspension of 6-methoxy-[1,5]naphthyridine-4-carbaldehyde (0.94 g, 5 mmol) in DCM (15 mL) at 0° C. The mixture was stirred at 0° C. for 1 h, diluted with DCM, washed with water, dried over MgSO4 and concentrated. Chromatography on SiO2 (Hex/EA 1:1) gave the product (25:1 Z/E mixture) as a colourless foam (1.92 g, 98% yield).

Provenance & Evidence