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

HRID 2163814Notes

Reaction equation

HRID 2163814 reaction equation
Cl.CO[C:4](=[O:9])[C@H:5]([CH3:8])NC.[C:10]([O:14][C:15](=[O:18])[CH2:16][CH3:17])(=O)CC.[CH2:19]([N:21](CC)CC)C.O>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:10][O:14][C:15](=[O:18])[C@H:16]([CH3:17])[N:21]([CH3:19])[C:4](=[O:9])[CH2:5][CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31263Propionic anhydrideHCID 13850987N-Methyl-L-alanine methyl ester hydrochloride (1:1)

Product 1

HCID 53825128N-methyl-N-propionyl-L-alanine methyl ester

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 150 ml of chloroform was dissolved 28 g (0.18 mol) of N-methyl-L-alanine methyl ester hydrochloride, followed by addition of 27 g (0.21 mol) of propionic anhydride and 33 ml of triethylamine. The mixture was allowed to stand at room temperature overnight. With the addition of 100 ml of water, the reaction mixture was stirred at room temperature for 30 minutes. Thereafter, 600 ml of ethyl acetate was added and the organic layer was washed with aqueous sodium hydrogen carbonate and water in the order mentioned, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. In the above manner, N-methyl-N-propionyl-L-alanine methyl ester was obtained as a yellow oil. NMR spectrum (CDCl3) δ: 1.15(3H,t,J=7Hz), 1.40(3H,d,J=7Hz), 2.40(2H,q,J=7Hz), 2.93(3H,s), 3.70(3H,s), 5.27(1H,q, J=7Hz)

Workup

  1. washthe organic layer was washed with aqueous sodium hydrogen carbonate and water in the order
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5c29aabdfa0c4027b6f87eb90a45d80e
Source dataset
uspto-grants-1979_01
Patent number
US04137230

Reaction notes

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