Sodium Hydroxide → isobutyl (4S)-4-benzyl-5-oxo-2-imidazolidinepropanoate

HRID 344747Notes

Reaction equation

HRID 344747 reaction equation
Cl.[NH2:2][C@H:3]([C:11]([NH2:13])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].O=[CH:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:21]>O>[CH2:4]([C@H:3]1[C:11](=[O:12])[NH:13][CH:17]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:21])[NH:2]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 10464575Isobutyl 4-oxobutanoateHCID 11953719L-Phenylalaninamide hydrochloride

Product 1

HCID 11722574isobutyl (4S)-4-benzyl-5-oxo-2-imidazolidinepropanoateYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of L-phenylalaninamide hydrochloride (20 g, 0.1 mol) in water (200 ml), adjusted to pH 8.2 with 10% sodium hydroxide (about 35 ml), was added isobutyl 4-oxobutanoate (16 g, 0.1 mol). The solution was refluxed for 24 hours After cooling, the solution was extracted with dichloromethane (4×200 ml). The organic phase was dried and evaporated to dryness under vacuum. The residue was chromatographed over silica gel (dichloromethanemethanol 9:1) to afford 6 g (20%) of the title compound, as an oil, which was characterized as the hydrochloride, m.p. 152°-155° C. (with decomposition) (after crystallization from ethanol-diethyl ether). NMR (DMSO-d6, CDCl13): deltaH =9.25 (b.s., 1H, CONH); 7.6-7.1 (c.a., 5H, PhH), 4.90 (t, J=6.1 Hz, 1H, NHCHNH); 4.17 (t, J=6.1 Hz, 1H, CHCH2Ph); 3.84 (d, J=6.9 Hz, 2H, COOCH2CH); 3.35 (c.a., 2H, CH2Ph); 2.50-1.60 (c.a., 5H, CH2CH2COO, CH2CH(CH3)2. MS (E.I., 70 eV, 1.5 mA) m/z=304 (M+), 213 (M--C7H7)+, 84 (C3H4N2O)+.

Workup

  1. temperatureThe solution was refluxed for 24 hours
  2. temperatureAfter cooling
  3. extractionthe solution was extracted with dichloromethane (4×200 ml)
  4. customThe organic phase was dried
  5. customevaporated to dryness under vacuum
  6. customThe residue was chromatographed over silica gel (dichloromethanemethanol 9:1)

Sources & evidence

ORD record
ord-5a6824f2087147369de7988c728074ed
Source dataset
uspto-grants-1991_10
Patent number
US05053422

Reaction notes

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