Water → HCID 86667485, compound

Participants

Reaction Conditions

Reaction Steps

The ethyl 4-(4-chlorobenzyl)-2-(morpholin-4-yl)-1,3-selenazole-5-carboxylate (35.0 mg, 0.0846 mmol) was placed in a round bottomed flask equipped with a stirbar. Tetrahydrofuran (1.00 mL) and methanol (0.1 mL) were added and the mixture was stirred to give a light yellow solution. A solution of lithium hydroxide in water (2.0 M, 0.423 mL, 0.846 mmol) was added in a single portion, and the resulting mixture was stirred under an atmosphere of nitrogen at room temperature overnight. LCMS analysis of the reaction indicated that starting material still remained; only a small amount of it had been hydrolyzed to the product. Additional tetrahydrofuran (2 mL) and lithium hydroxide in water (2.0 M, 0.423 mL, 0.846 mmol) were added and the reaction was heated overnight at 50° C. under an atmosphere of nitrogen. LCMS analysis indicated that the reaction was 90% complete. The reaction was heated at 60° C. for a further 8 hours. LCMS analysis indicated complete hydrolysis. The reaction was cooled to room temperature, diluted with 10 ml saline, and acidified with dilute acetic acid with good stirring. A white precipitate formed which became granular with stirring. The product was isolated on a fitted funnel, washed with water, and dried at 40° C. overnight to yield 29.2 mg (89% yield) product as a white powder. LC/MS (FA) ES+ 385/387/389. 1H NMR (400 MHz, DMSO) δ 12.73-12.44 (br s, 1H), 7.36-7.24 (m, 4H), 4.26-4.18 (s, 2H), 3.74-3.63 (t, J=4.8 Hz, 4H), 3.49-3.39 (t, J=4.7 Hz, 4H).

Provenance & Evidence