HCID 86745116, compound → HCID 19770791, compound

HRID 654112Notes

Reaction equation

HRID 654112 reaction equation
C(OC([N:11]1[CH2:15][C:14](=[O:16])[NH:13][CH:12]1/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[O:20])=O)C1C=CC=CC=1>C(O)C.[Pd]>[O:16]=[C:14]1[CH2:15][NH:11][CH:12]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[O:20])[NH:13]1

Participants

4

Reactant 1

HCID 86745116HCID 86745116, compound

Product 1

HCID 19770791HCID 19770791, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of isobutyl (E)-1-benzyloxycarbonyl-4-oxo-2-imidazolidineacrylate (7.7 g, 22.2 mmol) in 96% ethanol (200 ml), 5% palladium on charcoal (0.5 g) was added and hydrogen was bubbled at 20° C. and at atmospheric pressure for 2 hours. Removal of the catalyst and evaporation of the solvent gave a residue which was triturated with diisopropyl ether to give 4.1 g (86%) of the title compound, m.p. 50°-52° C. NMR (CDCl3): deltaH =4.45 (t, J=6 Hz, 1H, N--CH--N), 3.10 (s, 2 H, N--CH2 --CO). MS (E.I., 70 eV, 1.5 mA) m/z=214 (M+), 157 (M--C4H9 +, 85 (M--C7H13O2 +.

Workup

  1. customhydrogen was bubbled at 20° C. and at atmospheric pressure for 2 hours
  2. customRemoval of the catalyst and evaporation of the solvent
  3. customgave a residue which
  4. customwas triturated with diisopropyl ether

Sources & evidence

ORD record
ord-b808b99d0d644127bb38dec6a696c92b
Source dataset
uspto-grants-1992_07
Patent number
US05130319

Reaction notes

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