Ethyl Acetate → HCID 178437010, compound

Participants

Reaction Conditions

Reaction Steps

A solution of dimethyl-1-diazo-2-oxopropylphosphonate (0.86 g) in dry methanol (20 ml) was added at R.T. to a solution of crude N-[1-(tert-Butyl-diphenyl-silanyloxymethyl)-1-methyl-2-oxo-ethyl]-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide in dry methanol (40 ml). The reaction medium was cooled down to 0° C. and Potassium carbonate (0.773 g) was added portion wise along with additional dry methanol (10 ml). The reaction mixture was allowed to warm up to R.T., further stirred for 16 hrs and then poured onto a mixture of ethyl acetate and brine. The two layers were separated and the aqueous layer was extracted thrice with ethyl acetate. The organic layers were combined, washed once with brine and then dried over sodium sulphate. After filtration and concentration under reduced pressure 1.84 g of crude mixture were isolated as a dark orange oil. The residue was purified by flash chromatography on silica gel (hexane/ethyl acetate) to give 1.523 g of N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-prop-2-ynyl]-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide as a yellow oil.

Provenance & Evidence