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

HRID 539012Notes

Reaction equation

HRID 539012 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](=[O:17])[NH:8][C@@H:9]([CH:14]([CH3:16])[CH3:15])[C:10](OC)=[O:11].CCN(CC)CC>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:10](=[O:11])[C@H:9]([CH:14]([CH3:16])[CH3:15])[NH:8][C:7]1=[O:17]

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 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (S)-methyl 2-(3-(2,4-dimethoxybenzyl)ureido)-3-methylbutanoate (1.00 g, 3.10 mmol) in MeOH (7.5 mL) and NEt3 (0.430 mL, 3.10 mmol) in a sealed vessel was placed in preheated sand bath (at 100° C.) and heated for 18 hours. The cooled reaction mixture was concentrated and the residue was taken up in ether, washed with water, dried over sodium sulfate and filtered. Purification of the crude material by column chromatography, eluting with 1-3% MeOH/dichloromethane, afforded (S)-3-(2,4-dimethoxybenzyl)-5-isopropylimidazolidine-2,4-dione as an ivory colored solid (0.640 g, 71%). LCMS (APCI+) m/z 293 [M+H]+.

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customPurification of the crude material by column chromatography
  7. washeluting with 1-3% MeOH/dichloromethane

Sources & evidence

ORD record
ord-550b81a359bd43658762b9d7412ba734
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

Loading…