Prednisone Impurity 13 Chemical Properties

Boiling point:

636.3±55.0 °C(Predicted)

Density 

1.53±0.1 g/cm3(Predicted)

pka

11.57±0.70(Predicted)

InChIKey

LTRVYEKAPGRFOX-WFWLZCIZNA-N

SMILES

C[C@]12C[C@H](O)[C@@]3([C@]4(C=CC(=O)C=C4CC[C@@]3([H])[C@]1([H])C[C@@H](O)[C@]2(O)C(=O)COC(=O)C)C)Br |&1:1,3,5,6,15,17,20,22,r|

Prednisone Impurity 13 Usage And Synthesis

Uses

(11β,16α)-21-(Acetyloxy)-9-bromo-11,16,17-trihydroxy-pregna-1,4-diene-3,20-dione is used as a reactant in the synthesis of triamcinolone acetonide, a synthetic corticosteroid used to treat skin conditions.

Synthesis

50.5 g of 2-((8S,10S,13S,14S,16R,17S)-16,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate was dissolved in 1500 ml of acetone, 70 ml of 5% perchloric acid was added, the temperature was lowered to 0°C with stirring, and 45 g of N-bromosuccinimide was added and stirred After the reaction was completed, 50 ml of 20% sodium sulfite aqueous solution was added, the acetone was concentrated, the water was separated, filtered, and dried to obtain 62 g of Prednisone Impurity 13 (9α-bromo-11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate).