Diethyl Ether → Boc-L-Lys(Z)-OMe

Participants

Reaction Steps

An ethyl ether solution of 1.48 g (3.9 mmol) of Nε -benzyloxycarbonyl-Nα -(tert-butoxycarbonyl)-L-lysine was combined with an ethyl ether solution of diazomethane at 0° C. The reaction mixture was evaporated to give a colorless oil in nearly quantitative yield (1.54 g). TLC Rf =0.38 (chloroform/ethyl acetate, 5:1). IR (neat) ν 3340, 1710, 1530 cm-1. NMR (CDCl3) δ 7.3 (5H, s), 7.25 (1H m), 5.05 (2H, s), 5.0 (1H, m), 4.1 (1H, m), 3.8 (3H, s), 3.1 (2H, m), 2.0-1.1 (6H, m), 1.4 (9H, s). The product has the structural formula: ##STR62##

Provenance & Evidence