Sodium Methoxide → HCID 54692324, compound

Participants

Reaction Steps

To a stirred solution of 2-(4-fluorobenzyl)-4-(2-hydroxyethyl)-7-isopropyl-1,6,8-trioxo-1,3,4,6,7,8-hexahydro-2H-pyrazino[1,2-c]pyrimidine-9-yl pivalate (Example 74, Step 2, 40 mg, 0.08 mmol) in methanol (0.5 mL) was added sodium methoxide (25 wt. % solution in methanol, 1.6 mL) and the mixture stirred at room temperature for 20 min. The reaction was quenched by dropwise addition of 1 N hydrochloric acid and the solvent was removed in vacuo. The resulting residue was taken up in methylene chloride, filtered, and the filtrate concentrated. The residue was purified by reverse phase preparative HPLC (95:5 to 5:95 A:B where A=0.1% TFA-H2O and B=0.1% TFA-MeCN over 30 min) to afford the title compound. 1H NMR (CD3OD, 400 MHz): δ 7.44-7.40 (m, 2 H), 7.13-7.08 (m, 2 H), 5.19-5.15 (m, 1 H), 4.92-4.75 (m, 2 H), 4.51 (d, J=14.4 MHz, 1 H), 3.75 (dd, J=3.8 MHz, 13.4 MHz, 1 H), 3.51 (dd, J=1.6 MHz, 13.6 MHz, 1 H), 3.42-3.30 (m, 2 H), 1.76-1.71 (m, 1 H), 1.62-1.57 (m, 1 H), 1.45 (d, J=7.2 MHz, 6 H). HRMS (FT/ICR) M+H: calcd for (C19H23FN3O5)+ 392.1616. found 392.1625.

Provenance & Evidence