1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178453613, compound

Participants

Reaction Steps

At 0° C. under N2, diisopropylethylamine (1.1 mL, 6.6 mmol) was added dropwise to a mixture of 1A (564 mg, 2.0 mmol), Boc-tranexamic acid (565 mg, 2.2 mmol), HOBt (297 mg, 2.2 mmol), and EDCI (422 mg, 2.2 mmol) in anhydrous DMF (15 mL). After addition, the mixture was slowly warmed to rt and stirred for 2 h. The reaction mixture was diluted with ethyl acetate, washed with water, 1.0 N HCl, sat. NaHCO3, and brine, dried over MgSO4, filtered, and concentrated. Chromatography on silica gel provided 1B as a light yellow solid. LC/MS m/z 521.1 (M+H)+. 1H NMR (400 MHz, CDCl3) δ: 0.8-0-1.0 (m, 2H), 1.45 (s, 9H), 1.25-1.45 (m, 2H), 1.70-1.85 (m, 2H), 1.90-2.05 (2H), 2.95 (2H), 3.05-3.25 (2H), 4.60 (s, broad, 1H), 5.55 (m, 1H), 5.75 (m, 1H), 6.8 (s, 1H), 7.1 (s, 1H), 7.15 (d, J=7.8 Hz, 2H), 7.2-7.35, (m, 3H).

Provenance & Evidence