Methyl Acrylate → HCID 22122213, compound

HRID 1859170Notes

Reaction equation

HRID 1859170 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][NH:9][C:8](=[O:12])[C:7]1=[O:13].N12CCCN=C1CCCCC2.[C:31]([O:35][CH3:36])(=[O:34])[CH:32]=[CH2:33]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:33][CH2:32][C:31]([O:35][CH3:36])=[O:34])[C:8](=[O:12])[C:7]1=[O:13]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 127069801-[(2,4-Dimethoxyphenyl)methyl]piperazine-2,3-dione

Product 1

HCID 22122213HCID 22122213, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g of 1-(2,4-dimethoxybenzyl)-2,3-dioxopiperazine, 0.28 ml of 1,8-diazabicyclo[5.4.0]-undec-7-ene, 0.34 ml of methyl acrylate and 10 ml of N,N-dimethylformamide was stirred at room temperature for 12 hours. Then, the solvent was distilled off under reduced pressure, after which the resulting residue was added to a mixed solvent of 30 ml of ethyl acetate and 30 ml of water, and the pH was adjusted to 3 with 2N hydrochloric acid. The organic layer was separated and the aqueous layer was extracted with three 30-ml portions of ethyl acetate. The combined organic layer was washed with water and then a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent; chloroform : methanol=20:1) to obtain 0.68 g of methyl 3-[4-(2,4-dimethoxybenzyl)-2,3-dioxopiperazin-1-yl]propionate as a colorless oil.

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure
  2. additionafter which the resulting residue was added to a mixed solvent of 30 ml of ethyl acetate and 30 ml of water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with three 30-ml portions of ethyl acetate
  5. washThe combined organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by a silica gel column chromatography (eluent; chloroform : methanol=20:1)

Sources & evidence

ORD record
ord-9639852bb15e444f81cf2227f48c877a
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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