N-Hydroxysuccinimide → HCID 59510880, compound

Participants

Reaction Steps

To a solution of 5 (5.36 g, 27.2 mmol) in dichloromethane (500 mL) was added N-hydroxysuccinimide (4.23 g, 36.7 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (6.89 g, 35.9 mmol), and the resulting reaction mixture was stirred under dinitrogen for 15 h. The reaction mixture was washed twice with a 0.01 N HCl solution (150 mL), dried over sodium sulfate, and concentrated under reduced pressure. Purification was performed using silica gel chromatography (1:49 methanol/dichloromethane) to yield 7.83 g (98%) of 6 as a tan solid. 1H NMR (300 MHz, CDCl3): δ=2.31 (s, 3H, C—CH3), 4.08 (s, 4H, CH2), 3.50 (s, 3H, N—CH3), 3.98 (s, 3H, O—CH3), 6.29 (s, 1H, CH); 13C NMR (75 MHz, CDCl3): δ=20.6 (C—CH3), 25.8 (CH2), 32.0 (N—CH3), 60.8 (O—CH3), 103.0 (CH), 122.8, 140.7, 148.8, 159.9, 160.3, 169.0; TLC: Rf=0.33 (1:19 methanol/dichloromethane); ESI-MS calcd for C13H14N2O6 [M+H]+: 295.0930. found 295.0931.

Provenance & Evidence