Sodium Hydroxide → 3-Isobutyl-tetrahydro-pyrrolo[1,2-a]imidazole-2,5-dione

HRID 15110

Reaction equation

HRID 15110 reaction equation
Cl.[NH2:2][CH:3]([C:8]([NH2:10])=[O:9])[CH2:4][CH:5]([CH3:7])[CH3:6].[OH-].[Na+].C([O:15][C:16](=O)[CH2:17][CH2:18][CH:19]=O)C>O>[CH2:4]([CH:3]1[N:2]2[C:16](=[O:15])[CH2:17][CH2:18][CH:19]2[NH:10][C:8]1=[O:9])[CH:5]([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 82395Ethyl 4-oxobutanoateHCID 128663002-Amino-4-methylpentanamide hydrochloride

Product 1

HCID 197707923-Isobutyl-tetrahydro-pyrrolo[1,2-a]imidazole-2,5-dioneYield 74.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of DL-leucinamide hydrochloride (1.5 g, 9 mmol) in water (40 ml), adjusted to pH 9.5 with 10% sodium hydroxide, ethyl-4-oxobutanoate (1 g, 7.5 mmol) was added. The mixture was placed in a microwave oven and refluxed for 1 hour. Water was then evaporated under vacuum and the residue was chromatographated over silica gel (CH2Cl2/MeOH/NH4OH 98/2/0.1) to afford 1.1 g of the title compound.

Workup

  1. additionwas added
  2. customThe mixture was placed in a microwave oven
  3. temperaturerefluxed for 1 hour
  4. customWater was then evaporated under vacuum

Sources & evidence

ORD record
ord-d2df26a4f3b342069645ec4d14109d98
Source dataset
uspto-grants-2010_06
Patent number
US07732473B2

Linked notes

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