isobutyl (4S)-4-benzyl-5-oxo-2-imidazolidinepropanoate → (3S)-3-Benzyl-2,5-dioxohexahydro-1H-pyrrolo[1,2-a]imidazole

HRID 654120Notes

Reaction equation

HRID 654120 reaction equation
[CH2:1]([C@H:8]1[C:12](=[O:13])[NH:11][CH:10]([CH2:14][CH2:15][C:16]([O:18]CC(C)C)=O)[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[CH2:1]([C@@H:8]1[N:9]2[C:16](=[O:18])[CH2:15][CH2:14][CH:10]2[NH:11][C:12]1=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 11722574isobutyl (4S)-4-benzyl-5-oxo-2-imidazolidinepropanoate

Product 1

HCID 10105256(3S)-3-Benzyl-2,5-dioxohexahydro-1H-pyrrolo[1,2-a]imidazoleYield 50.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of isobutyl (4S)-4-benzyl-5-oxo-2-imidazolidinepropanoate (2.3 g, 7.33 mmol) in toluene (100 ml) was refluxed for 8 days. After evaporation of the solvent, the residue was chromatographed over silica gel (dichlorometane-methanol 9:1). The appropriate fractions were collected and evaporated; the residue was triturated with diethyl ether to afford 850 mg (50%) of the title compound, m.p. 141°-145° C. NMR (CDCl3): deltaH =7.25 (s, 5H, PhH); 7.02 (b.s., 1H, NH); 4.52 (t, J=4.5 Hz, 1H, PhCH2CH); 4.37 (t, J=5 Hz, 1H, NCHNH); 3.13 (d, J=4.5 Hz, 2H, PhCH2); 2.80-1.6 (c.a., 4H, CH2CH2). MS (E.I., 70 eV, 1.5 mA) m/z 230 (M+), 139 (M--C7H7)+, 91 (C7H7)+, 84 (C4H6NO)+.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was chromatographed over silica gel (dichlorometane-methanol 9:1)
  3. customThe appropriate fractions were collected
  4. customevaporated
  5. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-43b2130d1a2d47dba314d5f2ecc725a0
Source dataset
uspto-grants-1992_07
Patent number
US05130319

Reaction notes

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