Tryptamine → L-Lysine

Participants

Reaction Steps

10 mmol of a methoxycarbonyl derivative of a basic amino acid with the L-configuration is dissolved in 30 ml of DMF, 3.2 g (20 mmol) of tryptamine, 1.54 g of HOBt (10 mmol, monohydrate) and 2.1 g of DCC (10.17 mmol) is added, and the mixture is stirred at the room temperature for 24 h. A DCU precipitate is then filtered off and the solvent evaporated. The oily residue is dissolved in 150 ml of ethyl acetate and washed with 150 ml of 10% aqueous Na2CO3, water, 1% citric acid (three times) and brine. The organic layer is dried (MgSO4), filtered and evaporated to dryness. The residue is purified by column chromatography (SiO2) with O:H phase 7:3+3% MeOH, to yield amide of tetrakis(methoxycarbonyl) derivative of lysine as a dark orange oil.

Provenance & Evidence