Triethylamine → (S)-3-(2,4-dimethoxybenzyl)-5-isopropylimidazolidine-2,4-dione

HRID 2401271Notes

Reaction equation

HRID 2401271 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][C:7]([NH:9][C@H:10]([C:14](OC)=[O:15])[CH:11]([CH3:13])[CH3:12])=[O:8].C(N(CC)CC)C>CO>[CH3:1][O:2][C:3]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:4]=1[CH2:5][N:6]1[C:14](=[O:15])[C@H:10]([CH:11]([CH3:13])[CH3:12])[NH:9][C:7]1=[O:8]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 2012917(S)-methyl 2-(3-(2,4-dimethoxybenzyl)ureido)-3-methylbutanoate

Product 1

HCID 67033852(S)-3-(2,4-dimethoxybenzyl)-5-isopropylimidazolidine-2,4-dioneYield 113.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl N-[(2,4-dimethoxybenzyl)carbamoyl]-L-valinate (4.2 g) and triethylamine (1.3 g) in methanol was stirred while heating to reflux for 5 hr. After the solvent was distilled off under reduced pressure, the residue was purified by column chromatography (NH silica gel cartridge, hexane/ethyl acetate) to afford (5S)-3-(2,4-dimethoxybenzyl)-5-(propan-2-yl)imidazolidine-2,4-dione (4.3 g).

Workup

  1. temperaturewhile heating
  2. temperatureto reflux for 5 hr
  3. distillationAfter the solvent was distilled off under reduced pressure
  4. customthe residue was purified by column chromatography (NH silica gel cartridge, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-803e802af82e4dabb2ef707af131234a
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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