Potassium Hydroxide → (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[2-methyl-1-oxo-1-(1-tritylpiperazin-2-yl)propan-2-yl]oxyiminoacetic acid

Participants

Reaction Steps

(Z)-2-Amino-α-[[1,1-dimethyl-2-oxo-2-(N-tritylpiperazinyl)ethoxy]imino]-4-thiazoleacetic acid, methyl ester (4.03 g, 6.75 mmol) was suspended in a solution of 0.90 g of potassium hydroxide in ethanol (22.5 ml) and water (1.8 ml), and stirred overnight at room temperature. The reaction was then heated to 60° C. for 30 minutes. Upon cooling to room temperature, water (22.5 ml) was added, and the reaction mixture was filtered through Celite. The filtrate was then acidified to pH 3 with 1N hydrochloride acid while cooling in ice, and the precipitate that formed was isolated by filtration. The precipitate was washed with water, ether and acetonitrile to yield 1.71 g of the title compound.

Provenance & Evidence