473273-04-0Relevant articles and documents
Corticosteroid decomposition via a mixed anhydride
Conrow, Raymond E.,Dillow, Glen W.,Bian, Liangqiao,Xue, Liang,Papadopoulou, Olga,Baker, John K.,Scott, Britt S.
, p. 6835 - 6836 (2002)
Oxidation of dexamethasone in an aqueous suspension by air during prolonged storage produces the 17α-formyloxy-17β-carboxylic acid 4. A pathway to 4 is proposed that involves Baeyer-Villiger-type oxidation of keto aldehyde 1 to mixed anhydride 5, followed by intramolecular formyl transfer. Synthetically, acid 3 was reacted with N,N′-carbonyldiimidazole followed by triethylammonium formate in order to generate the transient anhydride 5 en route to an authentic sample of 4.