Thiazole → HCID 59831170, compound

Participants

Reaction Conditions

Reaction Steps

This example illustrates the preparation of the compounds of formula III, via the procedure described in the Application of Berkoz, Lewis and Muchowski, Ser. No. 706,412, filed on even date herewith. In this example 0.012 mole of sodium hydride (50% mineral oil) is stirred in 50 ml. of tetrahydrofuran; under nitrogen, and 0.02 mole of 5-hydroxymethyl-N-t-butyloxazolidine is added. The mixture is then warmed to 50° C until reaction ceases (about 30 minutes) and then cooled to room temperature. 0.01 Mole of 2-ethylsulfinyl-5-[2-(endobicyclo[3.1.0]hex-6-yl)ethylaminocarbonyl]thiazole in 50 ml. of tetrahydrofuran is then added. The mixture is stirred for four hours at room temperature and then poured into 200 ml. of ethyl acetate, then washed with water; dried over anhydrous magnesium sulfate and filtered. The filtrate is evaporated under vacuum affording a crude residue of 5-(5-[2-endobicyclo[3.1.0]hex-6-yl)ethylaminocarbonyl]thiazol-2-yloxy)methylene-N-t-butyloxazolidine, which is then dissolved in diethyl ether (100 ml.) and hydrogen chloride gas passed over the surface with rapid stirring until no more precipitate is formed. The precipitate is filtered off, washed with ether, then recrystallized from propanol-diethyl ether mixture. The crystals are filtered off and dried under vacuum affording 5-(5-[2-endobicyclo[3.1.0]hex-6-yl)ethylaminocarbonyl]thiazol-2-yloxy)methylene-N-t-butyloxazolidine hydrochloride.

Provenance & Evidence