Sodium → HCID 59558452, compound

Reaction equation

[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]([NH:8][C:9]1([CH2:12][CH:13]=[O:14])[CH2:11][CH2:10]1)=[O:7])C.[Na]>C1(C)C=CC=CC=1.CO>[CH3:1][O:3][C:4]([CH:5]1[C:13](=[O:14])[CH2:12][C:9]2([CH2:11][CH2:10]2)[NH:8][C:6]1=[O:7])=[O:15]

Participants

Procedure

N-[1-(2-Oxo-ethyl)-cyclopropyl]-malonamic acid ethyl ester (200 mg; 0.823 mmol) in toluene (3 ml) is added to a solution of sodium (18.9 mg; 0.823 mmol) in MeOH (1 ml). The reaction mixture is refluxed for 45 minutes, poured on water and washed with TBME. The aqueous phase is acidified with 2N HCl (0.2 ml) and evaporated to dryness to yield the title compound as yellow resin (162 mg; 100%). 1H-NMR (400 MHz; DMSO-d6): 8.39 (s, 1H); 3.73 (s, 3H); 3.18 (s, 1H); 2.48 (s, 2H); 0.76 (m, 2H); 0.64 (m, 2H). MS (m/z) ES+: 198 (MH+).