Dichloromethane → HCID 69029027, compound

Participants

Reaction Steps

A solution of amine 6 (17.8 mg, 0.04 mmol) in 1 M aqueous solution of NaHCO3 (1 mL) was treated with methoxycarbonylmaleimide (37.94 mg, 0.24 mmol) at 0° C. After 5 min, the mixture was diluted with water (1 mL) and acetonitrile (2 mL), and then stirred at room temperature for 4 h. After adding CH2Cl2 (50 mL), the organic layer was separated and washed with brine (3×10 mL). The organic layer was then dried (Na2SO4), filtered, and concentrated. The oily residue was purified by flash chromatography (CH2Cl2/MeOH 95:5) to give maleimide 7 (23.2 mg, 76%); Rf 0.42 (CH2Cl2/MeOH 95:5); 1H-NMR (CDCl3/TMS): δ6.70 (s, 2H, CH═CH), 6.69 (s, 4H, CH═CH), 6.68 (s, 2H, CH═CH), 4.98 (d, 1H, J=3.4 Hz, H-1), 3.95-3.82 (m, 2H, H-4, and OCHHCH2CH2N), 3.80˜3.35 (m, 22H, H-2, H-3, H-5, H-6, H-6′, OCH2CH2CH2N, OCH2CH2CH2N, and OCH2CH3), 1.96-1.78 (m, 8H, OCH2CH2CH2N), 1.25 (t, 3H, J=7.1 Hz, OCH2CH3); ES-MS: 779.28 (M+Na)+, 401.29 (M+2Na)2+.

Provenance & Evidence