Ethanethiol → HCID 54120511, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethanethiol (2.9 ml, 0.04 mole) and triethylamine (5.6 ml, 0.04 mole) in tetrahydrofuran (50 ml.) was added to n-butyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (14.3 g, 0.04 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 (6.8 ml, 0.08 mole) in 50 ml. of tetrahydrofuran. After stirring for 16 hours at 25° C., the solution was filtered and the filtrate concentrated in vacuo. The residual oil was dissolved in 100 ml. methylene chloride and washed with 3% hydrochloric acid, 3% ammonium hydroxide and saturated sodium chloride solution. Concentration in vacuo afforded an oil which was chromatographed on silica gel eluting with ethyl acetate-cyclohexane (1:1) to afford n-butyl N-trifluoroacetyl-N-(isopropylamino(ethylthio)phosphonomethyl)glycinate (0.7 g) as a white solid, m.p. 64°-65° C.

Provenance & Evidence