1-Butanol → Boc-3-nitro-L-tyrosine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.36 g (6.00 mmol) of 3-nitro-L-tyrosine in 30 mL of 1N NaOH, 1.74 g (8.00 mmol) of (BOC)2O in 8 mL of tent-butanol was added. The stiffing was continued overnight and the tert-butanol was removed in vacuo. Ethyl acetate (25 mL) was added to the residual aqueous layer and the resulting solution was cooled to 0° C. A solution of 1N KHSO4 was used to acidify the solution to pH 2 and the aqueous layer was separated and extracted with 25 mL of ethyl acetate (2×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to afford 0.265 g (13%) of the title compound as yellow solid.

Provenance & Evidence