Water → HCID 60206173, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of tert-butyl[4-(4-chlorophenyl)-2-isobutyl-1-oxo-6-trifluoromethanesulfonyloxy-1,2-dihydro-3-isoquinolinyl]methylcarbamate (Example 186 (1)) (2.06 g, 3.5 mmol), butyl acrylate (0.76 ml, 5.3 mmol), sodium hydrogencarbonate (0.45 g, 5.3 mmol), tetrabutylammonium chloride (0.11 g, 0.4 mmol) and palladium acetate (0.09 g, 0.4 mmol) in N,N-dimethylformamide (20 ml) was stirred with heating at 100° C. under an argon atmosphere for 48 h. The reaction mixture was poured into water and extracted with ethyl acetate. After washing the extract with water, the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give butyl (E)-3-[3-[[(tert-butoxycarbonyl)amino]methyl]-4-(4-chlorophenyl)-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinyl]-2-propenate (0.48 g, 23.8%) as crystals.

Provenance & Evidence