Hydrochloric Acid → Boc-homophenylalaninal

Participants

Reaction Steps

Morpholinecarbonylphenylalanine (2.74 g, 9.82 mmol, prepared according to the method described in Esser, R. et.al., Arthritis & Rheumatism (1994), 0000) was dissolved in THF (50 mL) at -10° C. 4-methylmorpholine (1.08 mL, 9.82 mmol) was added, followed by isobutyl chloroformate (1.27 mL, 9.82 mmol). The mixed anhydride was stirred for 10 minutes, whereupon a solution of ethyl (S)-4-amino-6-phenyl-2-hexenoate hydrochloride from the previous step in DMF (10 mL) was added, followed by 4-methylmorpholine (1.08 mL, 9.82 mmol). The mixture was stirred for 1 hour. 1M HCl (50 mL) was added. The product was extracted with ethyl acetate (100 mL), washed with saturated aqueous NaHCO3 (50 mL), dried over MgSO4 and decolorizing charcoal (DARCO), filtered, and evaporated to dryness, giving 3.80 g (80% yield from Boc-homophenylalaninal).

Provenance & Evidence