HCID 11294345, compound → HCID 87150482, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of acryl amide 2 (2 g 4.2 mmol) in a MeNO2/CHCl3 mixture (1:1; 100 mL), TMG 200 μL) was added and maintained at 25° C. for 24 h. The mixture was then concentrated in vacuo to give a crude solid, which was dissolved in CHCl3 then sequentially washed with dilute aqueous HCl, water, and saturated brine. The organic solution was dried (Na2SO4), filtered, and concentrated in vacuo to give a crude oil, which was column chromatographed (SiO2) eluting with 25% ethyl acetate (EtOAc) in hexane to give (93%) amide 3, as a white solid: 2.1 g; mp 140-141° C.; 1H NMR δ 1.45 (s, 27H, CH3), 1.99 (t, 6H, J=7.5 Hz, CH2CH2CO), 2.24 (t, 6H, J=7.5 Hz, CH2CO), 2.26 (m, 4H, CH2CH2CO), 4.47 (t, 2H, J=6 Hz, O2NCH2), 6.19 (s, 1H, N); 13C NMR δ 22.8 (CH2CO), 27.7 (CH3), 29.6 (CH2CO), 29.8 (CH2CH2CO), 32.4 (O2NCH2CH2), 57.3 (NHC), 74.5 (O2NCH2), 80.2 (CMe3), 170.1 (CONH), 172.4 (CO2); IR 3300, 1710, 1670, 1552 cm−1; MS ESI; 553.3, Calculated 553.3 [M+Na+]. Analysis (C26H46N2O9) Found C, 57.94; H, 8.66; N, 5.20. Calculated C, 58.85; H, 8.74; N, 5.28.

Provenance & Evidence