Trifluoroacetic acid → HCID 71513400, compound

Participants

Reaction Steps

To a solution of 1-tert-butyl 4-(4-(((3R,4R)-4-(3,4-dimethoxybenzyl)-2-oxotetrahydrofuran-3-yl)methyl)-2-methoxyphenyl) piperazine-1,4-dicarboxylate (155 mg, 0.27 mmol, 1.0 eq) in DCM (5 mL) was added TFA (1 mL). The resulting mixture was stirred at rt for 3 h, concentrated, basified by sat. NaHCO3, and extracted with DCM (30 mL×3). The combined organic layers were dried over MgSO4, filtered and concentrated to afford 4-(((3R,4R)-4-(3,4-dimethoxybenzyl)-2-oxotetrahydrofuran-3-yl)methyl)-2-methoxyphenyl piperazine-1-carboxylate (76.5 mg, 59.5%). LRMS (M+H+) m/z calculated 485.2, found 484.9. 1H NMR (CDCl3, 400 MHz) δ 6.98 (d, 1H), 6.74-6.78 (m, 2H), 6.65-6.68 (m, 1H), 6.51-6.56 (m, 2H), 4.13-4.17 (m, 1H), 3.83-3.90 (m, 1H), 3.85 (s, 3H), 3.83 (s, 3H), 3.77 (s, 3H), 3.53-3.66 (m, 4H), 2.90-2.97 (m, 6H), 2.48-2.69 (m, 4H).

Provenance & Evidence