Acetyl chloride → HCID 16222233, compound

Participants

Reaction Steps

To a solution of (R)-2-tert-butyl 1-methyl 6-(5-amino-2-chlorobenzyloxy)-3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate (15 mg, 0.033 mmol) in CH2Cl2 (1 mL) was added TEA (200 μl, 1.43 mmol) followed by the addition of acetyl chloride (10 μl, 0.05 mmol). The reaction was stirred at room temperature for 2 h. It was concentrated and purified by preparative HPLC (Phenomenex 20×100 mm eluting with 0-100% MeOH/H2O (90% in H2O, 0.1% TFA) gradient over 8 min with flow rate 25 mL/min) to yield (R)-2-tert-butyl 1-methyl 6-(5-acetamido-2-chlorobenzyloxy)-3,4-dihydroisoquinoline-1,2(1H)-dicarboxylate as a colorless oil (2 mg, 13%). HPLC retention time (Method C)=3.86 min. LC/MS (ESI) (M+H)+=489.12. 1H NMR (400 MHz, CDCl3) δ ppm 1.47 (s, 5H), 1.50 (s, 4H), 2.19 (s, 3H), 2.80-2.90 (m, 2H), 3.64-3.83 (m, 5H), 3.88 (s, 1H), 5.10 (s, 2H), 5.38 (s, 0.5H), 5.55 (s, 0.5H), 6.72-6.79 (m, 1H), 6.81-6.89 (m, 1H), 7.31-7.68 (m, 4H).

Provenance & Evidence