Diethyl (ethoxymethylene)malonate → HCID 58783534, compound

HRID 1374864Notes

Reaction equation

HRID 1374864 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH:8]([C:12](=[NH:21])[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].C([O:25][CH:26]=[C:27]([C:33](OCC)=O)[C:28]([O:30][CH2:31][CH3:32])=[O:29])C>CO>[CH2:31]([O:30][C:28]([C:27]1[C:26](=[O:25])[N:13]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:12]([CH:8]([NH:7][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:22])[CH:9]([CH3:11])[CH3:10])=[N:21][CH:33]=1)=[O:29])[CH3:32]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 178449790HCID 178449790, compound

Product 1

HCID 58783534HCID 58783534, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

Following the procedure of Veale, J. Org. Chem., 58,4490 (1993), to [1-(N-Benzyl-carbamimidoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester (10.86 g, 35.6 mmol) in methanol (160 mL) was added diethyl ethoxymethylenemalonate (7.7 g, 35.6 mmol). The reaction is equipped with a Dean-Stark trap. The reaction was heated at 100° C. until all solvent was removed. The residue was dissolved in methylene chloride, washed with 1 N HCl and water, dried (Na2SO4), and concentrated. The resulting pale yellow syrup was used in the next step without further purification.

Workup

  1. customThe reaction is equipped with a Dean-Stark trap
  2. customwas removed
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed with 1 N HCl and water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe resulting pale yellow syrup was used in the next step without further purification

Sources & evidence

ORD record
ord-a0975d42f14c4426b0a3400e57269a85
Source dataset
uspto-grants-2007_01
Patent number
US07166595B2

Reaction notes

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