Dicyclohexylcarbodiimide → HCID 86750401, compound

HRID 974862Notes

Reaction equation

HRID 974862 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([O:23][NH:24][C@H:25]([C:30]([NH:32][CH:33]([C:39]([O-:41])=O)[C:34]([O:36][CH2:37][CH3:38])=[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.[CH3:50][O:51][C:52]1[CH:53]=[C:54]([CH:57]=[CH:58][CH:59]=1)[CH2:55][NH2:56]>O1CCOCC1>[CH2:16]([O:23][NH:24][C@H:25]([C:30]([NH:32][CH:33]([C:39](=[O:41])[NH:56][CH2:55][C:54]1[CH:57]=[CH:58][CH:59]=[C:52]([O:51][CH3:50])[CH:53]=1)[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:31])[CH2:26][CH:27]([CH3:28])[CH3:29])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 211563-MethoxybenzylamineHCID 80170N-HydroxysuccinimideHCID 86750402HCID 86750402, compound

Product 1

HCID 86750401HCID 86750401, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.03 g of dicyclohexylcarbodiimide was added to 30 ml of a solution of 1.83 g of ethyl N-(N-benzyloxyleucyl)aminomalonate, 0.58 g of N-hydroxysuccinimide and 1.3 ml of (3-methoxybenzyl)amine in anhydrous dioxane. The mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered to remove-the insoluble materials. The filtrate was diluted with 100 ml of ethyl acetate. The resulting 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. 1.49 g of the resulting yellow oily substance was purified by silica gel column chromatography (eluant: ethyl acetate/n-hexane=1/2)to obtain 0.96 g of ethyl N-(N-benzyloxyleucyl)-α-[N-(3-methoxybenzyl)carbamoyl]glycinate as a colorless oily substance.

Workup

  1. filtrationThe reaction mixture was filtered to remove-the insoluble materials
  2. additionThe filtrate was diluted with 100 ml of ethyl acetate
  3. washThe resulting solution was washed with 1N hydrochloric acid
  4. 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
  5. distillationsubjected to distillation
  6. customto remove the solvent
  7. custom1.49 g of the resulting yellow oily substance was purified by silica gel column chromatography (eluant

Sources & evidence

ORD record
ord-7e3ac3335fbe496ea961bc110840068c
Source dataset
uspto-grants-1997_03
Patent number
US05607934

Reaction notes

Loading…