Tetrahydrofuran → Ethyl (tert-butoxycarbonyl)-D-methionylglycinate

Participants

Reaction Conditions

Reaction Steps

In 100 ml of THF are dissolved 10.0 g of BOC-(D)-Met-OH and 7.9 g of HONB, and after cooling to 0° C., 9.0 g of DCC is added. The mixture is stirred at 0° C. for 6 hours. The insolubles are filtered off, 5.9 g of H-Gly-OEt.hydrochloride and 5.6 ml of TEA are added to the filtrate and the mixture is stirred at room temperature overnight. The THF is distilled off and the residue is extracted with 100 ml of AcOEt, washed with water and dried over anhydrous sodium sulfate. The AcOEt is distilled off and the residue is crystallized from petroleum benzine and further recrystallized from AcOEt-petroleum benzine. Yield 9.8 g; m.p. 55°-56° C.; Rf1 =0.70; [α]D21 +12.5° (c=0.67, DMF).

Provenance & Evidence