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

HRID 848054Notes

Reaction equation

HRID 848054 reaction equation
[C:1]([O:4][C:5](=O)C)(=[O:3])C.[CH2:8]([N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])C.O.C(=O)([O-])[OH:17].[Na+]>C(Cl)(Cl)Cl>[CH3:5][O:4][C:1](=[O:3])[C@H:13]([CH3:14])[N:10]([C:11](=[O:17])[CH3:12])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic Anhydride2×HCID 8471TriethylamineHCID 516892Sodium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In 300 ml of chloroform is dissolved 33.7 g (0.22 mole) of N-methyl-L-analine methyl ester.hydrochloride, followed by the addition of 65 ml of acetic anhydride and 110 ml of triethylamine. The mixture is allowed to stand at a room temperature for 24 hours and, after the excess of acetic anhydride is decomposed with water, is neutralized with sodium hydrogen carbonate. The chloroform layer is separated and, the water layer is extracted with ethyl acetate (120 ml×5), followed by combining the chloroform and ethyl acetate layers to concentrate under reduced pressure. The brown, oily substance obtained is dissolved in chloroform, washed with aqueous sodium hydrogen carbonate and concentrated under reduced pressure. By the above procedure, there is obtained 31.8 g of N-acetyl-N-methyl-L-alanine methyl ester as brown oil.

Workup

  1. customThe chloroform layer is separated
  2. extractionthe water layer is extracted with ethyl acetate (120 ml×5)
  3. concentrationto concentrate under reduced pressure
  4. customThe brown, oily substance obtained
  5. washwashed with aqueous sodium hydrogen carbonate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-61e22076f527453781f300b89ac83afa
Source dataset
uspto-grants-1981_10
Patent number
US04294757

Reaction notes

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