反应详情

Ex-8c) 14.1 g of 1-Amino-4-chloro-2-butyne hydrochloride was taken up in 70 mL of dioxane and :35 mL water. 4 g NaOH was added and the reaction mixture was stirred for 30 minutes followed by the addition of 21.8 g di-t-butylcarbonate at 20° C. The reaction mixture was stirred at 20° C. to 25° C. for 8 h and then the lower organic layer was separated. The upper aqueous layer was extracted with 100 mL of dichloromethane. Organic layers were combined and washed with 50% aqueous NaHCO3, dried over anhydrous MgSO4, treated with Darco, filtered over celite and concentrated to give a brown oil. This oil was chromatographed to give 9 g of 1-t-Butyloxycarbonylamino-4-chloro-2-butyne as a white solid.

1. stirringThe reaction mixture was stirred at 20° C. to 25° C. for 8 h
2. customthe lower organic layer was separated
3. extractionThe upper aqueous layer was extracted with 100 mL of dichloromethane
4. washwashed with 50% aqueous NaHCO3
5. dry with materialdried over anhydrous MgSO4
6. additiontreated with Darco
7. filtrationfiltered over celite and
8. concentrationconcentrated
9. customto give a brown oil
10. customThis oil was chromatographed