Isobutyraldehyde → 2-Methylpropyl 3-carbamoylmethyl-Beta-hydroxy2-(1-methylethyl)-4-oxo-1-imidazolidinebutanoate

HRID 621601Notes

Reaction equation

HRID 621601 reaction equation
C(O)(=O)C.[NH2:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([NH2:13])=[O:12])=[O:8].[CH:14](=O)[CH:15]([CH3:17])[CH3:16].C(=O)([O-])[O-].[Na+].[Na+].[O:25]1[CH2:35][CH:26]1[CH2:27][C:28]([O:30][CH2:31][CH:32]([CH3:34])[CH3:33])=[O:29]>CO.O>[C:11]([CH2:10][N:9]1[C:7](=[O:8])[CH2:6][N:5]([CH2:35][CH:26]([OH:25])[CH2:27][C:28]([O:30][CH2:31][CH:32]([CH3:34])[CH3:33])=[O:29])[CH:14]1[CH:15]([CH3:17])[CH3:16])(=[O:12])[NH2:13]

Participants

7

Reactant 4

HCID 6561IsobutyraldehydeHCID 10340Sodium CarbonateHCID 5463767Isobutyl 3,4-epoxybutyrateHCID 19850195Glycylglycinamide acetate

Product 1

HCID 146180242-Methylpropyl 3-carbamoylmethyl-Beta-hydroxy2-(1-methylethyl)-4-oxo-1-imidazolidinebutanoate

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.91 g (0.01 mol) of glycylglycinamide acetate and 0.72 g (0.01 mol) of isobutyraldehyde in 40 ml of methanol was stirred for 24 hours at room temperature. The solvent was evaporated under reduced pressure and the residue was dissolved in 30 ml of isopropanol and treated with 0.106 g of sodium carbonate, 1.8 g (0.0115 mol) of 2-methylpropyl 3,4-epoxybutanoate and 2 drops of water. The mixture was refluxed for 36 hours. After evaporation of the solvent the residue was chromatographed on a silica gel column, eluting with dichloromethane/methanol 9:1. The title compound (0.48 g) was constituted by two diastereoisomers.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in 30 ml of isopropanol
  3. temperatureThe mixture was refluxed for 36 hours
  4. customAfter evaporation of the solvent the residue
  5. customwas chromatographed on a silica gel column
  6. washeluting with dichloromethane/methanol 9:1

Sources & evidence

ORD record
ord-753f2223352b4ab9a69f29d159f20695
Source dataset
uspto-grants-1989_04
Patent number
US04824861

Reaction notes

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