Sodium Hydroxide → (2S)-2-(32-chloro-4-methyl-20,28-dioxa-5,7,8,25-tetrazaheptacyclo[23.6.2.16,9.110,14.115,19.02,7.029,33]hexatriaconta-1(32),2,4,6(36),8,10,12,14(35),15(34),16,18,22,29(33),30-tetradecaen-3-yl)-2-[(2-methylpropan-2-yl)oxy]acetic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of (2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(3′-(allyloxy)-[1,1′-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (40 mg, 0.058 mmol) and Hoveyda-Grubbs 2nd generation catalyst (4.90 mg, 5.77 μmol) catalyst in DCE (2 mL) was heated at 50° C. for 5 h. Mixture was then cooled to room temp and concentrated under reduced pressure. Mixture was then treated with 1N NaOH (0.173 mL, 0.173 mmol) in MeOH (2.0 mL) at 50° C. for 3 h. Mixture was then cooled to room temp and purified by prep-HPLC to afford desired product (10 mg, 0.015 mmol, 26.6% yield) as inseparable mixture of cis and trans isomers. Used as is in the next step without further purification. LCMS (M+H)=651.3.

Provenance & Evidence