Trifluoroacetic acid → Methyl (2,3-dioxopiperazin-1-yl)acetate

HRID 1859171Notes

Reaction equation

HRID 1859171 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:8](=[O:17])[C:7]1=[O:18].FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[O:17]=[C:8]1[C:7](=[O:18])[NH:6][CH2:11][CH2:10][N:9]1[CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 53656911HCID 53656911, compound

Product 1

HCID 45115681Methyl (2,3-dioxopiperazin-1-yl)acetateYield 77.4%

Procedure

A mixture of 10.5 g of methyl [4-(2,4-dimethoxybenzyl)-2,3-dioxopiperazin-1-yl]acetate, 42 ml of trifluoroacetic acid and 21 ml of anisole was refluxed for 4 hours. The reaction mixture was cooled to room-temperature and then distilled under reduced pressure to remove the solvent. The resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=6:1) to obtain 4.5 g of methyl (2,3-dioxopiperazin-1-yl)acetate as colorless crystals.

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureThe reaction mixture was cooled to room-temperature
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent
  5. customThe resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=6:1)

Sources & evidence

ORD record
ord-f7d202a4092140dcb9e98ea8128f87bb
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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