Triethylamine → Glycine, N-(methoxyacetyl)-, ethyl ester

HRID 1675198Notes

Reaction equation

HRID 1675198 reaction equation
C(N(CC)CC)C.Cl.[CH2:9]([O:11][C:12](=[O:15])[CH2:13][NH2:14])[CH3:10].[CH3:16][O:17][CH2:18][C:19](Cl)=[O:20]>C(Cl)(Cl)Cl>[CH2:9]([O:11][C:12](=[O:15])[CH2:13][NH:14][C:19](=[O:20])[CH2:18][O:17][CH3:16])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 4777941Glycine, N-(methoxyacetyl)-, ethyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-78 °C

Procedure

1.5 ml of triethylamine was added to 500 mg of amino-acetic acid ethylester hydrochloride dissolved in 5 ml of chloroform, and the solution was cooled to −78° C. 0.34 ml of methoxyacetylchloride diluted with 3 ml of chloroform was slowly added thereto, and the resulting solution was heated slowly to room temperature and reacted for 6 hours. The reacted solution was washed with distilled water, adjusted to pH 8 to 9 by adding saturated sodium bicarbonate solution, extracted with organic solvent, dried over magnesium sulfate, and filtered and distilled under a reduced pressure to obtain the title compound (595 mg, 75%).

Workup

  1. additionwas slowly added
  2. temperaturethe resulting solution was heated slowly to room temperature
  3. customreacted for 6 hours
  4. washThe reacted solution was washed with distilled water
  5. additionby adding saturated sodium bicarbonate solution
  6. extractionextracted with organic solvent
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-40284933fc274addb72cefdc1b9fe455
Source dataset
uspto-grants-2011_08
Patent number
US08003658B2

Reaction notes

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