Triethylamine → Boc-L-Lys(Z)-OMe

Participants

Reaction Steps

Boc-Lys(Cbz)-OH (25 g) was dissolved in dichloromethane/methanol=9/1 v/v (500 ml). TBTU (21.1 g) was added and the solution adjusted to pH 8 by addition of triethylamine. The reaction mixture was stirred for 1 h at room temperature. The mixture was washed successively with cold 2N hydrogen chloride solution, water, 5% sodium hydrogencarbonate, and water. The organic layer was dried over sodium sulfate, filtered and evaporated. The residue was purified by chromatography on silica (eluent: ethyl acetate/heptane =1/4 v/v) to yield Boc-Lys(Cbz)-OMe (26.7 g). TLC: Rf=0.79, silica gel, ethyl acetate/heptane=3/1 v/v.

Provenance & Evidence