Phthalimide → 2-[(R)-2-(N-tert-butyloxycarbonylamino)-1-propylamino]benzothiazole

Participants

Reaction Conditions

Reaction Steps

2-[(R)-N-tertobutyloxycarbonylamino]-1-propylamine was prepared by standard synthetic steps from (R)-2-(N-tert-butyloxycarbonylamino)-1-propanol by Mitsunobu reaction with phthalimide followed by reaction with hydrazine hydrate. This amine (0.52 g, 3.0 mmol) and 2-chlorobenzothiazole (0.76 g, 4.5 mmol) were dissolved in dioxan (20 ml) and triethylamine (0.83 ml, 6.0 mmol) was introduced. The reaction mixture was heated at 50° C. for 18 h, evaporated and purified by "flash" column chromatography, eluting with heptane/ethyl acetate (10:3) to provide the 2-[(R)-2-(N-tert-butyloxycarbonylamino)-1-propylamino]benzothiazole (0.09 g, 10%) as an oil, TLC Rf 0.31 [SiO2 ; hexane/ethyl acetate (10:3)].

Provenance & Evidence