N-acetyl-N-methyl-L-alanine methyl ester → N-Acetyl-N-methyl-L-alanine

HRID 848055Notes

Reaction equation

HRID 848055 reaction equation
C[O:2][C:3](=[O:11])[C@H:4]([CH3:10])[N:5]([C:7](=[O:9])[CH3:8])[CH3:6]>CO.[OH-].[Na+]>[C:7]([N:5]([CH3:6])[C@H:4]([C:3]([OH:11])=[O:2])[CH3:10])(=[O:9])[CH3:8]

Participants

4

Reactant 1

HCID 54357781N-acetyl-N-methyl-L-alanine methyl ester

Product 1

HCID 13094160N-Acetyl-N-methyl-L-alanine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The ester obtained above is dissolved in a mixture of 100 ml methanol and 170 ml 1 N-aqueous sodium hydroxide. The solution is allowed to stand at a room temperature for 2 hours, and the methanol is removed under reduced pressure. The alkaline aqueous solution is extracted with chloroform. The water layer is brought to pH 1 with concentrated hydrochloric acid under ice-cooling and extracted with ethyl acetate (140 ml×5). The extract is dried over anhydrous sodium sulfate and concentrated under reduced pressure to recover a white solid. Recrystallization from ethyl acetate-hexane yields 8.1 g of N-acetyl-N-methyl-L-alanine as colorless needles.

Workup

  1. customthe methanol is removed under reduced pressure
  2. extractionThe alkaline aqueous solution is extracted with chloroform
  3. temperaturecooling
  4. extractionextracted with ethyl acetate (140 ml×5)
  5. dry with materialThe extract is dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto recover a white solid
  8. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-07dfd0ab72c5455698d1ffe2f8d37b74
Source dataset
uspto-grants-1981_10
Patent number
US04294757

Reaction notes

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