Sodium Carbonate → HCID 68052017, compound

Participants

Reaction Conditions

Reaction Steps

The product of Step 4 (HOAc salt; 3.49 g, 12.2 mmol) was added to a flask, followed by THF (55 mL). Aqueous sodium carbonate (2M; 30.5 mL, 60.9 mmol) was added, and the resulting biphasic mixture was cooled to 0° C. Benzyl chloroformate (2.61 mL, 18.3 mmol) was added and the reaction mixture was allowed to stir while the bath naturally warmed to ambient temperature. After 30 minutes the reaction mixture was partitioned between EtOAc and water (100 mL each) and the layers were separated. The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo to a crude oil that was purified by column chromatography on silica gel eluting with EtOAc/hexane (5-30%) (TLC was visualized with CAM staining) to afford the title product as a colorless oil. LRMS calc'd for C20H28N2O4Na [M+Na]+, 383; found 383. 1H NMR (500 MHz, CDCl3) δ 7.39-7.30 (br m, 5H), 5.15 (br s, 2H), 4.70-4.45 (br m, 1H), 4.15-3.95 (br m, 1H), 3.82-3.62 (br d, 1H), 3.50-3.21 (br m, 2H), 2.79 (br pentet, 1H), 2.30-1.90 (br m, 3H), 1.72-1.58 (br m, 1H), 1.45 (s, 9H), 1.40 (br m, 1H), 1.28-1.14 (br m, 1H).

Provenance & Evidence