Acetone → Anecortave Acetate

참여 물질

반응 조건

반응 단계

17α-hydroxy-20-phenoxypregna-4,9(11),20-trien-3-one (4.05 grams, 10 mmoles) is slurried with 210 ml of an aqueous pH 8 potassium phosphate buffer (0.5M in PO4 ≡), 20 ml of acetone, 40 ml of toluene/methylene chloride (3:2) and n-tetrabutylammonium bromide is (0.645 grams, 2.0 mmole) added. The pH is adjusted to 7.0 to 8.0 and the mixture cooled to 15° C. and an OXONE® solution is (18.4 gms, 30 mmoles dissolved in 65 ml of water) added dropwise by an addition funnel while stirring and maintaining pH at 7.0 to 8.0 by addition of a 30% potassium hydroxide solution. The reaction is worked up by separating the layers and replacing the organic solvent with toluene to a volume of 100 ml so as to remove water. After cooling to 10° C., 3 ml of glacial acetic acid is added. The product is isolated by replacing the toluene with acetone and filtering to obtain 3.12 g of 17α-hydroxy-21-acetoxypregna-4,9(11)-diene-3,20-dione.

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