Potassium Carbonate → Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-fluoroethoxy)pyridin-2-yl]methyl}-L-glutamate

Participants

Reaction Steps

To a solution of 196 mg 1-fluoro-2-iodoethane (1.13 mmol) in N,N-dimethylformamide (25 mL) was subsequently added 363 mg potassium carbonate (2.63 mmol), followed by 350 mg di-tert-butyl (4R)—N-(tert-butoxycarbonyl)-4-[(5-hydroxypyridin-2-yl)methyl]-L-glutamate 0.75 mmol), and the resulting mixture was stirred for 4 h at room temperature. The mixture was than partitioned between water and dichloromethane, and the organic layer was washed with brine, dried over magnesium sulfate, and evaporated. Purification of the crude product by preparative HPLC (method A) gave 313 mg of the target compound (81% yield).

Provenance & Evidence