Hydrochloric Acid → HCID 14715871, compound

HRID 971987Notes

Reaction equation

HRID 971987 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].Cl.C(N(CC)CC)C.[O:17]=[C:18]1[CH2:22][CH2:21][CH2:20][N:19]1[CH2:23][C:24](O)=[O:25].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.C(O)(=O)C>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][C:24](=[O:25])[CH2:23][N:19]1[CH2:20][CH2:21][CH2:22][C:18]1=[O:17])[CH3:3]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2723640Glycine ethyl ester, hydrochlorideHCID 31466872-(2-Oxopyrrolidin-1-yl)acetic acid

Product 1

HCID 14715871HCID 14715871, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

167.4 g (1.2 mole) of glycine ethyl ester hydrochloride are suspended in 4 liters of methylene chloride, the hydrochloric acid being neutralized by adding 168 ml (1.2 mole) of triethylamine. The reaction mixture is cooled to about 0° C. and a suspension of 171.6 g (1.2 mole) of 2-oxo-1-pyrrolidineacetic acid in 1500 ml methylene chloride is added. Without allowing the temperature to rise above 5° C., a solution of 272 g (1.4 mole) of DCC in 300 ml of methylene chloride is added dropwise to this mixture. Stirring is maintained for 2 hours at the same temperature and the reaction mixture is then allowed to return to ambient temperature, while stirring for 16 hours. 80 ml of acetic acid are then added, the reaction mixture is cooled to 0° C. and the precipitate is filtered off. The filtrate is evaporated to dryness and the residue redissolved in ethyl acetate, followed by filtering to remove insoluble matter. The filtrate is treated with highly absorbing active charcoal (Norite), again filtered and the filtrate is distilled at 190° C. at a pressure of 0.01 mm Hg. There are thus obtained 256 g of a syrup which is stirred with 1500 ml of anhydrous diethyl ether and which is crystallized by cooling in an ice bath. 177.5 g of N-(2-oxo-1-pyrrolidineacetyl)-glycine ethyl ester are thus obtained (yield: 64% of theory); M.P. 63°-64° C. The melting point of a sample recrystallized from a 1:2 v/v mixture of ethyl acetate and anhydrous diethyl ether is 64°-65° C.

Workup

  1. additionis added
  2. customto rise above 5° C.
  3. temperatureis maintained for 2 hours at the same temperature
  4. customto return to ambient temperature
  5. stirringwhile stirring for 16 hours
  6. temperaturethe reaction mixture is cooled to 0° C.
  7. filtrationthe precipitate is filtered off
  8. customThe filtrate is evaporated to dryness
  9. dissolutionthe residue redissolved in ethyl acetate
  10. filtrationby filtering
  11. customto remove insoluble matter
  12. additionThe filtrate is treated
  13. customwith highly absorbing active charcoal (Norite)
  14. filtrationagain filtered
  15. distillationthe filtrate is distilled at 190° C. at a pressure of 0.01 mm Hg
  16. stirringis stirred with 1500 ml of anhydrous diethyl ether and which
  17. customis crystallized
  18. temperatureby cooling in an ice bath

Sources & evidence

ORD record
ord-79b4e151e35042f28efa58d5b01f1a14
Source dataset
uspto-grants-1979_07
Patent number
US04162325

Reaction notes

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