Isoamyl Nitrite → HCID 131711529, compound

Participants

Reaction Conditions

Reaction Steps

pGlu-Ala-Lys(Xys)-Ser(Bzl)-Gln-Gly-Gly-NHNH2 (140 mg) is dissolved in dimethylformamide (5 ml). While the solution is cooled to -70° C., 6.51 N HCl-dioxane (0.05 ml) and isoamylnitrite (0.02 ml) are added. The mixture is stirred at -30° C. for 35 minutes and cooled again to -70° C., followed by addition of triethylamine (0.05 ml). HCl-H-Ser-Asn-OBut which is prepared by reducing Z-Ser-Asn-OBut (123 mg) is dissolved in dimethylformamide (2 ml) and this solution is added to the mixture, followed by addition of triethylamine (0.05 ml). The mixture is stirred between -15° C. and 5° C. for 30 hours. Insolubles are filtered off and the filtrate is distilled to evaporate the solvent. Ether is added and resulting powder is collected by filtration. Into a mixture of the powder and anisole contained in a cylinder of teflon resin, is introduced hydrogen fluoride (5 ml) and the mixture is stirred at 0° C. for one hour. Immediately the hydrogen fluoride is distilled off under reduced pressure and the residue is extracted twice-with water (10 ml each). The aqueous extract is washed three times with ether (3 ml each) and passed through a column (1.5×10 cm) of Amberlite IRA-410 (acetate form).

Provenance & Evidence