Hydrochloric Acid → HCID 70603825, compound

Participants

Reaction Steps

In this preparation 2.5 g. of benzhydryl 3-formyl-7β-(thiophen-2-yl-acetamido)-ceph-2-em-4-carboxylate in 50 ml. of anhydrous tetrahydrofuran is stirred under nitrogen at -70° C and 10 ml. of a 2.5 molar solution of vinyl magnesium-chloride is added dropwise over 5 minutes. After 15 minutes, 50 ml. of pH 7-buffer solution of dibasic sodium phosphate and monobasic potassium phosphate is added to the well stirred mixture, and then warmed to room temperature. The mixture is diluted with 200 ml. of water and layered with 200 ml. of ethyl acetate. The pH of the aqueous layer is adjusted to pH 4 by the addition of 20% aqueous hydrochloric acid. The ethyl acetate layer is separated and the aqueous layer extracted with 100 ml. ethyl acetate. The ethyl acetate extracts are combined and then washed twice with 50 ml. portions of brine, dried over sodium sulfate and evaporated under reduced pressure affording benzhydryl 3-(1-hydroxyprop-2-enyl)-7β -(thiophen-2-yl-acetamido)-ceph-2-em-4-carboxylate as a pale yellow oil (2.7 g.).

Provenance & Evidence