Water → HCID 178500545, compound

HRID 654994Notes

Reaction equation

HRID 654994 reaction equation
[H-].[Na+].[C:3]([C:6](=[C:11]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:7]([O:9][CH3:10])=[O:8])(=[O:5])[CH3:4].[CH3:25]I.O>O1CCCC1.C(OCC)(=O)C>[C:3]([C:6](=[C:11]([NH:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH:12]([CH3:25])[C:13]([O:15][CH3:16])=[O:14])[C:7]([O:9][CH3:10])=[O:8])(=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178500781HCID 178500781, compound

Product 1

HCID 178500545HCID 178500545, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under nitrogen stream, 60 % sodium hydride (1.68 g; 42 mmole) was added to dry tetrahydrofuran (10 ml), and a solution of dimethyl 2-acetyl-3-benzylamino-2-pentenedioate (6.2 g; 20 mmole) in dry tetrahydrofuran (40 ml) was portionwise added thereto with ice-cooling, followed by stirring at the same temperature for 15 minutes. Methyl iodide (5.68 g; 40 mmole) was added thereto at room temperature, and the resultant mixture was stirred at room temperature for 1 hour and at 40° C. for 1 hour. Water was added to quench the reaction, and the reaction mixture was diluted with ethyl acetate. The organic layer was washed successively with water, dilute hydrochloric acid and an aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give dimethyl 2-acetyl-3-benzylamino-4-methyl-2-pentenedioate.

Workup

  1. temperaturewith ice-cooling
  2. customto quench
  3. customthe reaction
  4. washThe organic layer was washed successively with water, dilute hydrochloric acid
  5. dry with materialan aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-adcd1f39887b472585f99f1c4f30769b
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

Loading…