Aminoacetaldehyde dimethyl acetal → N-(Ethyl carboxymethyl)-N'-(2,2-dimethoxyethyl)oxamide

HRID 990704Notes

Reaction equation

HRID 990704 reaction equation
[CH2:1]([CH:3]([C:12]([OH:14])=[O:13])[NH:4][C:5](=[O:11])[C:6]([O:8]CC)=O)[CH3:2].[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][NH2:19]>CC(O)C>[CH2:1]([CH:3]([C:12]([OH:14])=[O:13])[NH:4][C:5]([C:6]([NH:19][CH2:18][CH:17]([O:20][CH3:21])[O:16][CH3:15])=[O:8])=[O:11])[CH3:2]

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 18621232Ethyl N-(ethyl carboxymethyl)oxamate

Product 1

HCID 18621234N-(Ethyl carboxymethyl)-N'-(2,2-dimethoxyethyl)oxamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of the oxamate 3 (84.0 g, 414 mmol) in 2-propanol (500 mL) was added aminoacetaldehyde dimethyl acetal 4 (45.7 g, 435 mmol) in one portion. After stirring overnight at room temperature, the reaction mixture was concentrated to a thick orange oil. This thick slurry was diluted with 2-propanol (300 mL) and the solid was broken up with a spatula. Filtration afforded a solid which was further rinsed with an additional portion of 2-propanol. Removal of residual 2-propanol was accomplished via high vacuum to afford a light orange solid 5.: 1H NMR (CDCl3) δ7.82 (br s, 1H), 7.50 (br s, 1H), 4.41 (t, 1H, 5.3 Hz), 4.24 (q, 2H, 2.71 Hz), 4.09 (d, 2H, 5.9 Hz), 3.47 (dd, 2H, 5.3, 6.2 Hz), 3.40 (s, 6H), 1.30 (t, 3H, 7.1 Hz).

Workup

  1. concentrationthe reaction mixture was concentrated to a thick orange oil
  2. additionThis thick slurry was diluted with 2-propanol (300 mL)
  3. filtrationFiltration
  4. customafforded a solid which
  5. washwas further rinsed with an additional portion of 2-propanol
  6. customRemoval of residual 2-propanol

Sources & evidence

ORD record
ord-2eaf135eb123428da34ae53ae4f5ed81
Source dataset
uspto-grants-2002_10
Patent number
US06462050B1

Reaction notes

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