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

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Reaction Steps

Di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-prop-2-yn-1-yl-L-glutamate (150 mg, 377 μmol) and 2-azidoethanol (49 mg, 566 μmol) were dissolved in tetrahydrofuran (3.75 ml). To the solution, copper(I) iodide (7.2 mg, 38 μmol) and N,N-diisopropylethylamine (79 μl, 453 μmol) were added and the mixture was stirred for 12 h at room temperature. The mixture was then concentrated in vacuo and the residue was purified by preparative reversed phase HPLC to yield 62 mg (34%) of the product.

Provenance & Evidence