p-Toluenesulfonic acid → HCID 90281991, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-[4-(benzyloxy)-2-chlorophenyl]ethanone (500 mg) and toluene (15.0 mL) were added p-toluenesulfonic acid (110 mg) and tert-butyl glycinate (0.800 mL), followed by heating at 120° C. for 18 hours. After completion, the reaction mixture was left to be cooled, and then concentrated under reduced pressure. To the residue was added methanol (10.0 mL), and the sodium borohydride (90.0 mg) was added there to under ice-cooling, followed by stirring under ice-cooling for 2 hours. To the reaction mixture were added a saturated aqueous ammonium chloride solution and ethyl acetate, and the organic layer was extracted. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl N-{1-[4-(benzyloxy)-2-chlorophenyl]ethyl}glycinate (560 mg).

Provenance & Evidence