Potassium Hydroxide → HCID 17851043, compound

HRID 1374995Notes

Reaction equation

HRID 1374995 reaction equation
C([O:3][C:4](=[O:25])[C:5]([NH:21][C:22](=[O:24])[CH3:23])([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([O:19][CH3:20])[CH:13]=1)C(OCC)=O)C.[OH-].[K+]>O.C(O)C>[C:22]([NH:21][CH:5]([C:4]([OH:25])=[O:3])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([O:19][CH3:20])[CH:13]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 13406780HCID 13406780, compound

Product 1

HCID 17851043HCID 17851043, compoundYield 106%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 2-acetylamino-2-(3-methoxy-4-methylbenzyl)-malonic acid diethyl ester (10.0 g), potassium hydroxide solution (1.88 g) in water (25 ml) and ethanol (25 ml) were stirred under reflux for 1 hour. Another potassium hydroxide solution (1.88 g) in water (10 ml) was added to the mixture and the whole was stirred under reflux for 2 hours. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. Water (50 ml) and ethyl acetate (50 ml) were added to the resulting aqueous solution. The aqueous layer was separated and was adjusted to pH 1.5 with 6N hydrochloric acid. The solution was extracted with ethyl acetate, washed with brine, dried over sodium sulfate and evaporated under reduced pressure to give N-acetyl-3-methoxy-4-methyl-DL-phenylalanine (7.58 g) as a viscous oil.

Workup

  1. temperatureunder reflux for 1 hour
  2. stirringthe whole was stirred
  3. temperatureunder reflux for 2 hours
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. additionWater (50 ml) and ethyl acetate (50 ml) were added to the resulting aqueous solution
  6. customThe aqueous layer was separated
  7. extractionThe solution was extracted with ethyl acetate
  8. washwashed with brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-40d21ff615ce438b82d43c5d9337f3cc
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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