Hydrochloric Acid → (6R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Participants

Reaction Steps

To a suspension of 7-phthalisoimido-3-methyl-3-cephem-4-carboxylate (172 mg., 0.5 mmol.) in tetrahydrofuran (7 ml.) at 0° was added anhydrous hydrazine (.032 ml., 1 mmol.). After 7 min., 1N HCl (2.5 ml.) and water (2.5 ml.) were added. The mixture was heated on a stream bath for 10 min. after which it was cooled and evaporated in vacuo to a volume of ca. 5 ml. The aqueous solution was filtered, and the pH of the filtrate was adjusted to 3.7 with 5% sodium bicarbonate solution. After 15 min. the solution was filtered giving 73 mg. (68%) of 7-amino-3-methyl-3-cephem-4-carboxylate. Spectral data as well as tlc data showed the product to be identical with an authentic sample of 7-ADCA.

Provenance & Evidence