Acetic Anhydride → N-acetyl-N-methyl-L-alanine methyl ester

HRID 2199076Notes

Reaction equation

HRID 2199076 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH3:8])[NH:6][CH3:7].[C:10](OC(=O)C)(=[O:12])[CH3:11].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.O>[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH3:8])[N:6]([C:10](=[O:12])[CH3:11])[CH3:7]

Participants

7

Reactant 4

HCID 7918Acetic Anhydride2×HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 13850987N-Methyl-L-alanine methyl ester hydrochloride (1:1)

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

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

Workup

  1. customThe chloroform layer was separated
  2. extractionthe water layer was extracted with ethyl acetate (120 ml×5)
  3. concentrationconcentrated under reduced pressure
  4. customThe brown oil thus obtained
  5. washwashed with aqueous sodium hydrogen carbonate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7eb2687ca6964cbca72dd7e7f1c2c324
Source dataset
uspto-grants-1982_11
Patent number
US04361650

Reaction notes

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