Tert-butoxycarbonylalanine → HCID 13079748, compound

Participants

Reaction Steps

1.14 g of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride were added with stirring under an inert atmosphere at 0° to 5° C. to a solution of 1.92 g of (20S) 3α-amino-5α-pregnan-20-ol, 2.27 g of tert.-butyloxycarbonyl-L-alaine (BOC-L-Alanine), 60 ml of chloroform and 12 ml of pyridine and the mixture was stirred for 75 minutes after which another 1.15 g of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride was added thereto. The mixture was stirred at 0° to 5° C. for 50 minutes and was evaporated to dryness. The residue was taken up in aqueous sodium bicarbonate solution and the solution was extracted with ethyl acetate. The organic phase was washed with aqueous saturated sodium chloride and then with aqueous N hydrochloric acid and then with aqueous saturated sodium chloride solution, dried and evaporated to dryness. The residue was crystallized from isopropyl ether and was vacuum filtered. The product was rinsed with isopropyl ether and dried at 60° C. under reduced pressure to obtain 2-[1,1-dimethylethoxycarbonylamino]-N-[(20S)-5α-pregnan-20-ol-3α-yl]-propanamide melting at 171° C.

Provenance & Evidence