1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 87834573, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 81B (370 mg, 1.25 mmol) and N-Boc-alanine (286 mg, 1.51 mmol) in dichloromethane (10 mL) was treated with 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide (361 mg, 1.88 mmol). The reaction was stirred for 15 minutes at 25° C. Dichloromethane (50 mL) was added and the resulting mixture was washed with saturated sodium carbonate (50 mL) and brine (50 mL). The organic layers were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 30% ethyl acetate in hexanes to provide 482 ng of the title compound (83%) as white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.26-1.35 (m, J=5.70, 5.70 Hz, 9H) 1.39 (s, 9H) 4.12-426 (m, 1H) 5.14-5.31 (m, 1 H) 6.86 (d, J=8.82 Hz, 1H) 7.05 (s, 2H) 7.37 (d, J=7.72 Hz, 1H) 7.83 (dd, J=9.19, 2.94 Hz, 1H) 7.87 (s, 1H) 8.26 (d, J=2.94 Hz, 1H); MS (ESI) m/z 466.0 (M+H)+.

Provenance & Evidence