Triethylamine → HCID 62231065, compound

HRID 1485124Notes

Reaction equation

HRID 1485124 reaction equation
CC1(C)O[C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[CH2:11](Cl)[CH3:12].[NH2:14][CH2:15][C:16]([OH:18])=[O:17].C(N(CC)CC)C.C(OCC)(=O)C>C(#N)C>[CH2:11]([O:17][C:16](=[O:18])[CH2:15][NH:14][C:7](=[O:8])[CH2:6][C:4]([OH:5])=[O:3])[CH3:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 88258111HCID 88258111, compound

Product 1

HCID 62231065HCID 62231065, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Meldrum's acid (10.0 g) in acetonitrile (231 mL), glycine ethyl hydrochloride (14.5 g) and triethylamine (14.1 g) were added and the mixture was stirred at 60° C. for 5 hours. After cooling the mixture to room temperature, ethyl acetate was added and extraction was conducted with a saturated aqueous solution of sodium hydrogencarbonate. To the combined aqueous layers, 1 mol/L hydrochloric acid was added and extraction was conducted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate. After removing the desiccant by filtration, the filtrate was concentrated under reduced pressure to give the titled compound as a colorless solid (7.95 g).

Workup

  1. temperatureAfter cooling the mixture to room temperature
  2. extractionextraction
  3. additionTo the combined aqueous layers, 1 mol/L hydrochloric acid was added
  4. extractionextraction
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. customAfter removing the
  7. filtrationdesiccant by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-54aa30f792b3495fbcffbd2b8f92cd20
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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