L-Tyrosine → HCID 3478588, compound

Participants

Reaction Steps

Thionyl chloride (4.6 mL, 63.33 mmol, 2 eq) was added dropwise to dry MeOH (65 mL) at 0° C. and stirred for 5 min. Tyrosine (5.70 g, 31.5 mmol, 1 eq) was then added and the reaction vessel was fitted with a drying tube filled with drierite and slowly allowed to come to room temperature over 21 h. The solvent was then evaporated and crude product dried over high vacuum for 8 h. The crude product was then dissolved in a 1:1 mixture of acetone (63 mL) and a 7% solution of Na2CO3 in water (63 mL). Benzyl chloroformate (4.7 mL, 34.7 mmol, 1.2 eq) was then added dropwise and the reaction was stirred for 3 h at room temperature. Ethyl acetate was then added (300 mL), and the organic layer was washed with water (100 mL), brine (100 mL) and dried over Na2SO4. The solvent was evaporated to give 10 as a viscous yellow oil (10.37 g). The product was used in the next step without purification.

Provenance & Evidence