Benzoyl chloride → HCID 20156122, compound

Participants

Reaction Steps

A suspension of [(2-aminoethyl)hydroxyphosphinyl]acetic acid (0.75 g., 4.49 mmole) in a mixture of dioxane (5 ml.) and water (5 ml.) was cooled in an ice bath and treated with triethylamine (2.0 ml., 14.5 mmole). A clear solution was obtained. The mixture was then treated with benzoyl chloride (0.65 ml., 5.6 mmole) dropwise over a 5 minute period. After stirring at 0° for one hour, the mixture was evaporated to dryness. The residue was taken up in saturated sodium bicarbonate (20 ml.) and washed with ethyl acetate. The aqueous phase was acidified with concentrated hydrochloric acid (pH 1) and extracted with dichloromethane. The dichloromethane extracts were discarded and the aqueous phase evaporated to a small volume. This was then applied to an AG 1-X8 (acetate form) column (30 ml. bed volume) eluting first with water then with 5% acetic acid-water then 1N hydrochloric acid. The product eluted with 1N hydrochloric acid. Fractions containing the product were combined, evaporated to dryness, taken up in water, and lyophilized. The crude product (0.9 g.) was chromatographed on an HP-20 column (1 inch diameter column, 200 ml. bed volume) eluting with a linear gradient of water-acetonitrile (0→100%) at a flow rate of 5 ml./min., collecting 5 ml. fractions. The fractions containing the desired product (Tlc) were combined, evaporated, taken up in water, millipore filtered, and lyophilized to give 0.72 g. of [[(2-benzoylamino)ethyl]hydroxyphosphinyl]acetic acid as a white solid; m.p. 54°-57°; Rf (isopropanol/conc. NH4OH/water; 7:2:1)=0.42.

Provenance & Evidence