Ethyl diazoacetate → HCID 66744808, compound

Participants

Reaction Steps

To a solution of tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-vinyl-pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (850 mg, 1.4 mmol) in toluene (0.2 mL) at 110° C. was added a solution of ethyl 2-diazoacetate (637 mg, 587 μL, 5.6 mol) in toluene (0.7 mL) slowly over a period of 30 minutes. The reaction mixture showed incomplete conversion to product, when stirred at room temperature, so another 4 equivalents of ethyl 2-diazoacetate (637 mg, 587 μL, 5.6 mmol) was added and the reaction mixture was heated at 110° C. for 20 minutes. The reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The residue obtained was purified via silica gel column chromatography using 5 to 100% EtOAc in hexanes to yield ethyl 2-[5-[bis(tert-butoxycarbonyl)amino]-6-[5-[4-[[tert-butoxycarbonyl(methyl)amino]methyl]phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]cyclopropanecarboxylate (921 mg, 1.326 mmol, 94.96%). LC/MS m/z 595.6 [M+H-Boc]+.

Provenance & Evidence