Pyridine → HCID 53793433, compound

Participants

Reaction Steps

To a solution of N-Boc-L-phenylalanine (2.0 g, 7.5 mmol) in CH2Cl2 (20 mL) at 0° C. was added DCC (780 mg, 3.8 mmol) in CH2Cl2 (20 mL) via cannula. The reaction mixture was stirred for 1 h, the precipitate filtered off, and the filterate concentrated to dryness. Acetamidoxime (195 mg, 2.64 mmol) and pyridine (20 mL) were added and the reaction mixture heated at reflux for 1.5 h and then at RT for 16 h. The reaction mixture was poured into EtOAc (50 mL) and washed with 10% citric acid (3×25 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification by column chromatography (25% EtOAc/hex) furnished (R)-[1-(3-methyl-[1,2,4]oxadiazol-5-yl)-2-phenylethyl]carbamic acid tertbutyl ester (790 mg, 99% yield). 304.22, M+H.

Provenance & Evidence