Sodium hydride → HCID 86743244, compound

Participants

Reaction Steps

Diethyl phosphite (8.9 ml., 69 mmole) is dissolved in dry tetrahydrofuran (125 ml.) under argon in a 250 ml. round-bottomed flask equipped with a condenser. Sodium hydride (2.4 g.) is added in small portions with frothing and bubbling. When the evolution of hydrogen ceases, the reaction mixture is heated to reflux for 45 minutes. It is then cooled to room temperature, and a solution of (S)-2-[[(4-methylphenyl)sulfonyl]amino]-1-hexanol, 4-methylbenzenesulfonate ester (18.1 mmole) is added dropwise over 5 minutes. A white solid precipitates. The mixture is then heated to reflux for 3.5 hours. It is cooled and partitioned between ethyl acetate and 5% potassium bisulfate. The ethyl acetate layer is washed with 5% potassium bisulfate, saturated sodium bicarbonate, and brine, and then concentrated in vacuo. The resulting gum is triturated with hexane to give 6.45 g. of beige solid (S)-[2-[[(4-methylphenl)sulfonyl]amino]hexyl]phosphonic acid, diethyl ester.

Provenance & Evidence