Chloroacetyl chloride → L-Alanine, N-(chloroacetyl)-, ethyl ester

HRID 2199023Notes

Reaction equation

HRID 2199023 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].Cl.[CH2:7]([O:9][C:10](=[O:14])[C@H:11]([CH3:13])[NH2:12])[CH3:8].[OH-].[Na+]>ClC(Cl)C>[CH2:7]([O:9][C:10](=[O:14])[C@H:11]([CH3:13])[NH:12][C:3](=[O:4])[CH2:2][Cl:1])[CH3:8]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)

Product 1

HCID 22822139L-Alanine, N-(chloroacetyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

A solution of 7.2 g (0.064 mole) of chloroacetyl chloride in 20 ml dichloroethane was added dropwise at 0°-5° C. to a rapidly stirred mixture of 10 g (0.064 mole) of the DL-alanine ethyl ester, hydrochloride prepared above and 10.2 g of 50% aqueous sodium hydroxide (0.128 mole) in 80 ml dichloroethane. The mixture was allowed to come to room temperature after addition was complete. After standing 3 hours the product was isolated by washing with 50 ml of saturated salt solution, dried over magnesium sulfate, followed by evaporation of the solvent. The product, 8.0 g was a solid having a m.p. of 43°-47° C. and was identified by nuclear magnetic resonance (NMR) and infrared (IF) spectroscopy analysis as the title compound.

Workup

  1. customto come to room temperature
  2. additionafter addition
  3. customthe product was isolated
  4. washby washing with 50 ml of saturated salt solution
  5. dry with materialdried over magnesium sulfate
  6. customfollowed by evaporation of the solvent

Sources & evidence

ORD record
ord-d8a3c0f1fffd4c20ab4301fd90f8ab8e
Source dataset
uspto-grants-1982_11
Patent number
US04361439

Reaction notes

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