Diisopropylethylamine → di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-[(1-{2-[(methylsulfonyl)oxy]ethyl}-1H-1,2,3-triazol-4-yl)methyl]-L-glutamate

Participants

Reaction Steps

Di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-prop-2-yn-1-yl-L-glutamate (60 mg, 151 μmol) and 2-azidoethyl methanesulfonate (37.4 mg, 226 μmol) were dissolved in tetrahydrofuran (4 ml). To the solution, copper(I) iodide (2.9 mg, 15 μmol) and N,N-diisopropylethylamine (32 μl, 181 μmol) were added and the mixture was stirred for 18 h at room temperature. The mixture was then concentrated in vacuo and the residue was purified by preparative reversed phase HPLC. The product fractions were collected, lyophilized, and purified again by silicagel chromatography to yield 50 mg (47%) of the product.

Provenance & Evidence