Benzaldehyde → HCID 22885226, compound

Participants

Reaction Steps

16.9 g (71.5 mmol) of tyrosine-tert-butyl ester and 8.33 g (78.6 mmol) of benzaldehyde are stirred in 50 ml of methanol for 3 hours at 24° C. and then mixed with 3.37 g (53.6 mmol) of sodium cyanoborohydride. After 24 hours of stirring at room temperature, the batch is adjusted to pH 2 by careful addition of semiconcentrated hydrochloric acid, then neutralized with concentrated aqueous sodium bicarbonate solution and, after substantial evaporation of methanol, it is shaken out with ethyl acetate. The organic phase is dried on anhydrous magnesium sulfate, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with diethyl ether/hexane/triethylamine; the product-containing fractions are combined and concentrated by evaporation.

Provenance & Evidence