Dicyclohexylcarbodiimide → HCID 54017655, compound

HRID 974861Notes

Reaction equation

HRID 974861 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([O:23][NH:24][C@H:25]([C:30]([OH:32])=O)[CH2:26][CH:27]([CH3:29])[CH3:28])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.ON1C(=O)CCC1=O.Cl.[NH2:42][CH:43]([C:49]([O:51][CH2:52][CH3:53])=[O:50])[C:44]([O:46][CH2:47][CH3:48])=[O:45]>O1CCOCC1.C(N(CC)CC)C>[CH2:16]([O:23][NH:24][C@H:25]([C:30]([NH:42][CH:43]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[C:49]([O:51][CH2:52][CH3:53])=[O:50])=[O:32])[CH2:26][CH:27]([CH3:28])[CH3:29])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)HCID 54555085HCID 54555085, compound

Product 1

HCID 54017655HCID 54017655, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent2×

Procedure

22.90 g of dicyclohexylcarbodiimide was added to 300 ml of a solution of 26.39 g of N-benzyloxyleucine and 13.35 g of N-hydroxysuccinimide in anhydrous dioxane. The mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered to remove the insoluble materials, whereby a colorless solution was obtained. Separately, 20 ml of triethylamine was added to 300 ml of a suspension of 28.57 g of diethyl aminomalonate hydrochloride in anhydrous dioxane. To the mixture was applied an ultrasonic wave for 1 hour. Thereto was added the above colorless solution. The mixture was stirred at room temperature for 16 hours and then at a bath temperature of 100° C. for 3.5 hours. The reaction mixture was subjected to distillation to remove the solvent. The residue was dissolved in 1,000 ml of ethyl acetate. The solution was washed with 1N hydrochloric acid, an aqueous solution saturated with sodium hydrogen carbonate and an aqueous solution saturated with sodium chloride in this order, then dried with anhydrous magnesium sulfate, and subjected to distillation to remove the solvent to obtain 39.22 g of diethyl N-(N-benzyloxyleucyl)aminomalonate as a yellow oily substance.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the insoluble materials, whereby a colorless solution
  3. customwas obtained
  4. customfor 1 hour
  5. additionThereto was added the above colorless solution
  6. stirringThe mixture was stirred at room temperature for 16 hours
  7. waitat a bath temperature of 100° C. for 3.5 hours
  8. distillationThe reaction mixture was subjected to distillation
  9. customto remove the solvent
  10. dissolutionThe residue was dissolved in 1,000 ml of ethyl acetate
  11. washThe solution was washed with 1N hydrochloric acid
  12. dry with materialan aqueous solution saturated with sodium hydrogen carbonate and an aqueous solution saturated with sodium chloride in this order, then dried with anhydrous magnesium sulfate
  13. distillationsubjected to distillation
  14. customto remove the solvent

Sources & evidence

ORD record
ord-283ada5a9da34d92b40c7153b13ace6f
Source dataset
uspto-grants-1997_03
Patent number
US05607934

Reaction notes

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