Dicyclohexylcarbodiimide → HCID 19969572, compound

HRID 974867Notes

Reaction equation

HRID 974867 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([O:23][NH:24][C@H:25]([C:30]([NH:32][CH:33]([C:37](=[O:48])[NH:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([O:46][CH3:47])[CH:41]=1)[C:34](O)=[O:35])=[O:31])[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>O1CCOCC1>[CH2:16]([O:23][N:24]1[CH:25]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:30](=[O:31])[NH:32][CH:33]([C:37](=[O:48])[NH:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([O:46][CH3:47])[CH:41]=2)[C:34]1=[O:35])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 53837496HCID 53837496, compound

Product 1

HCID 19969572HCID 19969572, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.41 g of dicyclohexylcarbodiimide was added to 20 ml of a solution of 0.91 g of N-(N-benzyloxyleucyl)-α-[N-(3-methoxybenzyl)]carbamoylglycine and 0.23 g of N-hydroxysuccinimide in anhydrous dioxane. The mixture was stirred at room temperature for 16 hours. The reaction mixture was filtered to remove the insoluble materials. The filtrate was diluted with 50 ml of ethyl acetate. The resulting solution was washed with 1N hydrochloric acid and an aqueous solution saturated with sodium hydrogen carbonate, then dried with anhydrous magnesium sulfate, and subjected to distillation to remove the solvent, to obtain 0.81 g of 1-benzyloxy-6-isobutyl-3-[N-(3-methoxybenzyl)]carbamoylpiperazine-2,5-dione as a mixture of a cis form and a trans form.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the insoluble materials
  3. additionThe filtrate was diluted with 50 ml of ethyl acetate
  4. washThe resulting solution was washed with 1N hydrochloric acid
  5. dry with materialan aqueous solution saturated with sodium hydrogen carbonate, then dried with anhydrous magnesium sulfate
  6. distillationsubjected to distillation
  7. customto remove the solvent

Sources & evidence

ORD record
ord-1fb1a42c7dda4fc79d6cbb5a423748d7
Source dataset
uspto-grants-1997_03
Patent number
US05607934

Reaction notes

Loading…