Benisone,Warner Lambert,US,1973
BETAMETHASONE BENZOATE (200 MG) is an analog of Betamethasone (B327000), a glucocorticoid used as an anti-inflammatory agent.
ChEBI: Betamethasone benzoate is a 21-hydroxy steroid.
A mixture of 50 g of betamethasone, 50 cc of dimethylformamide, 50 cc of
methyl orthobenzoate and 1.5 g of p-toluenesulfonic acid is heated for 24
hours on oil bath at 105°C while a slow stream of nitrogen is passed through
the mixture and the methanol produced as a byproduct of the reaction is
distilled off. After addition of 2 cc of pyridine to neutralize the acid catalyst the
solvent and the excess of methyl orthobenzoate are almost completely
eliminated under vacuum at moderate temperature. The residue is
chromatographed on a column of 1,500 g of neutral aluminum oxide. By
elution with ether-petroleum ether 30 g of a crystalline mixture are obtained
consisting of the epimeric mixture of 17α,21-methyl orthobenzoates. This
mixture is dissolved without further purification, in 600 cc of methanol and
240 cc of methanol and 240 cc of aqueous 2N oxalic acid are added to the
solution. The reaction mixture is heated at 40°-50°C on water bath, then
concentrated under vacuum, The residue, crystallized from acetone-ether,
gives betamethasone 17-benzoate, MP 225°-231°C.
Poison by subcutaneous route.An experimental teratogen. Other experimentalreproductive effects. When heated to decomposition itemits toxic fumes of F-.
