(S)-ethyl 2-(2-((2-allylbenzamido)methyl)-7-(4-(allyloxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate → ethyl (2S)-2-(tert-butoxy)-2-[(20E)-4,24-dimethyl-12-oxo-23-oxa-1,5,7,8,11-pentaazapentacyclo[22.2.2.16,9.02,7.013,18]nonacosa-2,4,6(29),8,13(18),14,16,20-octaen-3-yl]acetate

Participants

Reaction Steps

To a stirred solution of (S)-ethyl 2-(2-((2-allylbenzamido)methyl)-7-(4-(allyloxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.058 g, 0.094 mmol) in 1,2-dichloroethane (20 mL) at 70° C. was added Hoveyda-Grubbs catalyst 2nd generation (2.94 mg, 4.69 μmol) and refluxed for 2 h. Then, cooled, concentrated and the resulting residue was purified by flash chromatography using 1:1 and 1:3 Hex/EtOAc to afford ethyl (2S)-2-(tert-butoxy)-2-[(20E)-4,24-dimethyl-12-oxo-23-oxa-1,5,7,8,11-pentaazapentacyclo[22.2.2.16,9.02,7.013,18]nonacosa-2,4,6(29),8,13(18),14,16,20-octaen-3-yl]acetate.

Provenance & Evidence