Isoamyl Nitrite → HCID 131713878, compound

Participants

Reaction Conditions

Reaction Steps

42.3 Milligrams of Z-Tyr-Ser-Leu-Ser-NHNH2 was dissolved in 4 ml of dimethylformamide, further 0.34 ml of 10-hold diluted-dimethylformamide solution of 6 NOhydrochloric acid/dioxane was added thereto, and the mixture was cooled to -15° C., then 0.091 ml of 10-hold diluted-dimethylformamide solution of isoamyl nitrite was added with stirring. After the reaction mixture shows a negative reaction in hydrazine-test, 0.29 ml of 10-hold diluted-dimethylformamide solution of triethylamine was added drop by drop in small amounts to neutralize the reaction mixture. This reaction mixture containing azide product was added to 4 ml of a cold dimethylformamide solution containing 50.0 mg of H-Thr-Asn-Leu-Gln-Glu-Ser-Leu-Arg-Ser-Lys(Tos)-Glu-OH and 0.1 ml of 10-fold diluted-dimethylformamide solution of triethylamine, then the whole mixture was stirred at -10° to -15° C. for 2 hours, next at 4° C. for 18 hours. Further, a product being converted 42.3 mg of Z-Tyr-Ser-Leu-Ser-NHNH2 into an azide was added thereto and was reacted for 24 hours. Dimethylformamide was removed by distillation under a reduced pressure, the residue obtained was extracted with 30 ml of n-butanol being saturated with water, the extract was washed 10 times with water being saturated with n-butanol, next washed 5 times with 2%-acetic acid being saturated with n-butanol. The organic layers were collected and subjected to distillation under a reduced pressure to remove n-butanol, then the residue was lyophilized, reprecipitated from ethyl acetate-ether to obtain the desired product.

Provenance & Evidence