Sodium Hydroxide → (2S)-2-(4,26-dimethyl-20,25-dioxa-1,5,7,8,11,12,13-heptazahexacyclo[24.2.2.16,9.111,14.115,19.02,7]tritriaconta-2,4,6(33),8,12,14(32),15(31),16,18-nonaen-3-yl)-2-[(2-methylpropan-2-yl)oxy]acetic acid

Participants

Reaction Steps

To a stirred solution of (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-((4-(3-(allyloxy)phenyl)-1H-1,2,3-triazol-1-yl)methyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.018 g, 0.027 mmol) in 1,2-dichloroethane (15 mL) was added at once Hoveyda-Grubbs catalyst 2nd generation (0.857 mg, 1.368 μmol) at 70° C. and refluxed for 2 h. Then, cooled, 10% Pd/C (2.91 mg, 2.74 μmol) was added and stirred under balloon H2 atmosphere for 5 h. Then, filtered, concentrated and the dark residue was refluxed with NaOH (0.137 ml, 0.137 mmol) in MeOH (2 mL) for 6 h. Then, cooled and purified by pre-HPLC to afford desired product (0.0064 g, 10.18 μmol, 37.2% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 8.44 (s, 1H), 7.77 (d, J=7.6 Hz, 1H), 7.38 (t, J=8.0 Hz, 1H), 7.16-7.20 (m, 1H), 6.90-6.95 (m, 1H), 6.61 (s, 1H), 5.73-5.87 (m, 3H), 4.24-4.37 (m, 2H), 4.16-4.23 (m, 1H), 3.73 (t, J=11.4 Hz, 1H), 3.49-3.59 (m, 3H), 3.03 (d, J=11.8 Hz, 1H), 2.59 (s, 3H), 1.88-2.04 (m, 4H), 1.74-1.82 (m, 2H), 1.52-1.72 (m, 2H), 1.26 (s, 3H), 1.25 (s, 9H). LCMS (M+H)=604.6.

Provenance & Evidence