Isopropanol → HCID 54565818, compound

Participants

Reaction Conditions

Reaction Steps

A solution of isopropanol (1.0 ml, 0.025 mole) and triethylamine (3.5 ml, 0.025 mole) in 50 ml. of tetrahydrofuran was added to a solution of β-chloroethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (9.1 g, 0.025 mole) in 250 ml. of ether at 0° C. After three hours, the solution was filtered and the filtrate was added to a cooled (0° C.) solution of isopropylamine (4.2 ml, 0.05 mole) in 50 ml. of tetrahydrofuran. After stirring for 16 hours at 25° C., the reaction mixture was filtered and the filtrate was concentrated in vacuo. The residual oil was dissolved in methylene chloride and washed with 3% hydrochloric acid, 3% ammonium hydroxide and saturated sodium chloride solution. The solution was dried over sodium sulfate and concentrated in vacuo to yield a solid. Recrystallization from ethyl acetate-hexane (1:10) yielded β-chloroethyl N-trifluoroacetyl-N-(isopropyl(isopropylamino)phosphonomethyl)glycinate as a white solid, m.p. 87.5°-89° C.

Provenance & Evidence