Methyl iodide → (S)-1-tert-Butyl 5-methyl 2-((tert-butoxycarbonyl)amino)pentanedioate

Beteiligte Stoffe

Reaktionsschritte

12.0 g of Boc-Glu-OtBu (39.6 mmol) are dissolved in 200 mL of DMF. Under argon atmosphere, 7.09 g of cesium carbonate (21.8 mmol, 0.55 eq.) are added and the resulting suspension is stirred for 1 hour at RT. After this time, 2.47 mL of methyl iodide (39.6 mmol) are added and stirred at RT overnight. The solvent is removed in vacuo and the obtained residue is taken up in 400 mL of ethyl acetate. The undissolved solid is filtered and the filtrate is washed with respectively 75 mL of 10% citric acid, 10% NaHCO3 solution and brine 3 times. After drying of the organic phase over Na2SO4 the solvent is removed in vacuo. The product is obtained as yellow oil. The product can be used without further purification in the following reaction.

Herkunft & Nachweise