Ethyl acetate hexane → Methyl (2S)-2-(tert-butoxy)-2-[(23Z)-4,27-dimethyl-26-oxa-1,5,7,8-tetraazahexacyclo[25.2.2.16,9.110,14.02,7.015,20]tritriaconta-2,4,6(33),8,10(32),11,13,15(20),16,18,23-undecaen-3-yl]acetate

Participants

Reaction Conditions

Reaction Steps

(S)-Methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2′-(but-3-en-1-yl)-[1,1′-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (116 mg, 0.182 mmol) was dissolved in DCE (150 mL). The solution was heated to 75° C. in an oil bath under an N2 atmosphere. Once the reaction flask had reached 75° C. the Hoveyda-Grubbs Catalyst 2nd generation (11.45 mg, 0.018 mmol) was added. The yellow reaction mixture turned green. Stirring at 85° C. was continued for 2 h at which time the reaction appeared complete by TLC (4:1 hexane/EtOAc) and HPLC (˜4:1 mixture of E/Z isomers). The cooled reaction mixture was concentrated in vacuo and purified by Biotage chromatography (0-50% EtOAc/hexanes) to give 84 mg of the desired product as a colorless oil. LCMS (M+H).=609.

Provenance & Evidence