Potassium Carbonate → HCID 66714132, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 10.6 g of tert-butyl 3-[(2-methanesulfonyloxy-ethyl)-(2-nitro-benzenesulfonyl)-amino]-propionate in 220 ml of DMF was added 16.2 g of K2CO3 and 5.6 g of diethyl 4-hydroxy-pyridine-2,6-dicarboxylate. The mixture was heated for 20 hours at 60° C. and then concentrated under reduced pressure and taken up in 200 ml of water and 200 ml of EtOAc. The aqueous phase was extracted 2× with EtOAc. The organic phases were combined, washed with saturated NaCl solution, dried over MgSO4, concentrated under reduced pressure and purified by flash chromatography on silica (Merck EasyVarioPrep 600 g column, Si60 15-40 μm), using a gradient of 0 to 20% EtOAc in DCM. The fractions containing the desired product were combined and concentrated under reduced pressure. 6.56 g of diethyl 4-{2-[(2-tert-butoxycarbonyl-ethyl)-(2-nitro-benzenesulfonyl)-amino]-ethoxy}-pyridine-2,6-dicarboxylate were obtained. LC/MS (C): tr=4.14 min; [M+H]+: m/z 596.

Provenance & Evidence