HCID 22289804, compound → HCID 87663615, compound

Participants

Reaction Steps

A solution of amine 8 (23.9 mg, 29.0 μmol) dissolved in 1 M aqueous solution of NaHCO3 (1 mL) was treated with methoxycarbonylmaleimide (27.03 mg, 17.4 μmol) 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 1 h. The mixture was diluted with CH2Cl2 (50 mL) and washed with brine (3×10 mL). The organic phase was dried over Na2SO4, filtered and concentrated. The oily residue was purified by flash chromatography (CH2Cl2/MeOH 96:4) to give maleimide 9 (20.3 mg, 71%); Rf 0.45 (CH2Cl2/MeOH 96:4); 1H-NMR (CDCl3/TMS): δ6.72 (s, 8H, CH═CH), 4.94 (d, 1H, J=3.4 Hz, H-1), 3.95-3.82 (m, 2H, H-4, and OCHHCH2CH2N), 3.80˜3.45 (m, 22H, H-2, H-3, H-5, H-6, H-6′, OCH2CH2CH2S, SCH2CH2N, and OCH2CH3), 2.90-2.60 (m, 16H, OCH2CH2CH2SCH2CH2N), 1.96-1.82 (m, 8H, OCH2CH2CH2S), 1.23 (t, 3H, J=7.1 Hz, OCH2CH3); ES-MS: 1019.49 (M+Na)+, 951(M-OEt)+.

Provenance & Evidence