Pentachlorophenol → Ethyl ((benzyloxy)carbonyl)-L-phenylalanylglycinate

Temperatur

50 °C

A solution of 6.0 (20 mM) N-carbobenzoxy-L-phenylalanine, 5.3 g (20 mM) pentachlorophenol, and 2.0 g (30 mM) isopropyl isonitrile in 40 ml chloroform was mixed with a solution of 2.8 g (20 mM) glycine ethyl ester hydrochloride and 2.02 g (20 mM) triethylamine in 30 ml chloroform. The mixture was heated at 50°C for 24 hours and evaporated. The residue was taken up in 150 ml ethyl acetate. The solution was washed sequentially with 100 ml water, 120 ml 1-N hydrochloric acid, 4 times 120 ml 5% sodium bicarbonate solution, and again with 100 ml water, then dried with desiccated sodium sulfate and evaporated. When the residue was crystallized from ethyl acetate and petroleum ether, 6.3 g N-carbobenzoxy-L-phenylalanyl-glycine ethyl ester was obtained (82% yield). Recrystallizing from ethyl acetate and petroleum ether reduced the yield to 5.4 g (70%). M.P. 107° - 108.5° C. [ α]D25 = - 17.1° (C = 2, in ethanol).

1. customevaporated
2. washThe solution was washed sequentially with 100 ml water, 120 ml 1-N hydrochloric acid, 4 times 120 ml 5% sodium bicarbonate solution
3. dry with materialagain with 100 ml water, then dried with desiccated sodium sulfate
4. customevaporated
5. customWhen the residue was crystallized from ethyl acetate and petroleum ether

ORD-Eintrag

ord-8eac8905b27c4eef9c3dbe86bcbb6138

Quelldatensatz

uspto-grants-1976_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US03984417