Sodium Carbonate → Zenuzolac

Participants

Reaction Steps

Benzaldehyde (1, 32.8 mmol) and hydroxylamine hydrochloride (33 mmol) were dissolved in methanol (100 ml) followed by addition of sodium carbonate (65 mmol). Overnight reaction gave the oxime derivative in 95% (2, 30.4 mmol). Chlorination of the oxime using N-chlorosuccinimide (31.6 mmol) in DMF (100 ml) quantitatively furnished chlorooxime (3). Compound 3 was then dissolved in THF/H2O (*0/20) and treated with 3-butenoate (24.5 mmol) and sodium carbonate (73.6 mmol). After completion, (12 h), the product was extracted with ethyl acetate and the organic extracts were washed with brine and dried over magnesium sulfate. GIT-27 was crystallized from ethyl acetate/heptane mixture. The structure was confirmed by 1H-NMR, 13C-NMR and mass spectroscopy. The daily dosage regimen will presumably vary within wide ranges, for instance from 0.1 to 10 mg/kg body weight.

Provenance & Evidence