Sodium → HCID 59558452, compound

HRID 1175144Notes

Reaction equation

HRID 1175144 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

5

Reactant 2

HCID 5360545SodiumHCID 86629356HCID 86629356, compound

Product 1

HCID 59558452HCID 59558452, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

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+).

Workup

  1. temperatureThe reaction mixture is refluxed for 45 minutes
  2. additionpoured on water
  3. washwashed with TBME
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-25e4654fb79d49e3adb26716aec926d2
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

Loading…