Citric Acid → HCID 10979461, compound

Participants

Reaction Steps

After dissolving ethyl 1-[2-[N-(diethylphosphonoacetyl)-N-[1-(S)-phenylethyl]amino]acetyl]cyclopropanecarboxylate (25.0 g, 55.2 mmol) in toluene (250 ml), tert-butoxypotassium (7.40 g, 66.2 mmol) was added gradually while stirring and cooling with ice. After stirring the reaction solution for 15 minutes at room temperature, a 10% aqueous citric acid solution (250 ml) and ethyl acetate (250 ml) were added thereto, and after performing an extraction operation, the organic layer was separated. The aqueous layer was then subject to extraction with ethyl acetate (250 ml), and after washing the combined organic layer with saturated sodium bicarbonate water (250 ml) and saturated saline solution (250 ml) in that order, the organic layer was dried over anhydrous sodium sulfate. After filtering, the filtrate was concentrated under a reduced pressure, the concentrate was applied to a silica gel chromatography, and 12.1 g (73%) of the title compound was obtained as a orange syrup from an n-hexane:ethyl acetate=2:1 to 1:2 eluate. The instrumental analysis data for this resulting compound agreed with the data indicated in PCT/JP96/00208.

Provenance & Evidence