Isobutyl 3-benzyl-5-oxo-2-imidazolidinepropanoate hydrochloride → Isobutyl 5-oxo-2-imidazolidinepropanoate hydrochloride

HRID 654124

Reaktionsgleichung

Reaktionsgleichung von HRID 654124
[ClH:1].C([N:9]1[CH2:13][C:12](=[O:14])[NH:11][CH:10]1[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:18])C1C=CC=CC=1.[H][H]>[Pd].O.CO>[ClH:1].[O:14]=[C:12]1[NH:11][CH:10]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:18])[NH:9][CH2:13]1

Komponenten

5

Edukt 2

HCID 19770783Isobutyl 3-benzyl-5-oxo-2-imidazolidinepropanoate hydrochlorideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 67886019Isobutyl 5-oxo-2-imidazolidinepropanoate hydrochlorideAusbeute 872,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

To a mixture of 10% palladium on charcoal (1 g) and 99% formic acid (1 ml) in methanol (25 ml), under nitrogen, was added a solution of isobutyl 3-benzyl-5-oxo-2-imidazolidinepropanoate hydrochloride (1 g, 2.93 mmol) and 99% formic acid (1.25 ml) in methanol (25 ml). The mixture was stirred under nitrogen for 6 hours. After addition of water (15 ml) and removal of the catalyst, the solvent was evaporated and the residue was triturated with ethanol to give 0.3 g (41%) of the title compound, m.p. 136°-140° C. The same compound was obtained also by the following procedure: into a mixture of isobutyl 3-benzyl-5-oxo-2-imidazolidinepropanoate hydrochloride (2.2 g, 6.4 mmol), and 10% palladium on charcoal (1.1 g) in water-methanol 2:1 (150 ml) hydrogen was bubbled at room temperature and at atmosphere pressure for 2 hours. Removal of the catalyst and evaporation of the solvent under reduced pressure gave a residue which was triturated with ethanol to afford 14 g (90%) of the title compound, m.p.136°-40° C. NMR (DMSO-d6): deltaH =11.1-9.50 (b.s., 2H, NH2+); 9.20 (b.s., 1H, CONH); 4.95 (t, J=6.2 Hz, 1H, NHCHNH); 3.84 (d, J=6.7 Hz, 2H, COOCH2); 3.65 (s, 2H, NCH2CO); 2.70-2.30 (c.a., 2H, CH2CH2COO); 2.25-1.60 (c.a., 3H, CH2CH2COO, CH(CH3)2); 0.87 (d, J=6.7 Hz, 6H, CH(CH3)2. MS (E.I., 70 eV, 1.5 mA) m/z=214 (M+), 141(M--OC4H9)+, 85 (C3H5N2O)+.

Aufarbeitung

  1. customThe same compound was obtained also by the following procedure
  2. customwas bubbled at room temperature and at atmosphere pressure for 2 hours
  3. customRemoval of the catalyst and evaporation of the solvent under reduced pressure
  4. customgave a residue which
  5. customwas triturated with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2b3b518e091446efa291e911654969ac
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05130319

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