Dicyclohexylcarbodiimide → HCID 88377736, compound

HRID 974863Notes

Reaction equation

HRID 974863 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([CH2:25][C:26](=[N:30][OH:31])[C:27]([OH:29])=O)=[CH:17]1.ON1C(=O)CCC1=O.Cl.[NH2:41][C@H:42]([C:47]([O:49][CH3:50])=[O:48])[CH2:43][CH:44]([CH3:46])[CH3:45]>O1CCOCC1.C(OCC)(=O)C.C(N(CC)CC)C>[OH:31][N:30]=[C:26]([CH2:25][C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:16][CH:17]=1)[C:27]([NH:41][C@H:42]([C:47]([O:49][CH3:50])=[O:48])[CH2:43][CH:44]([CH3:46])[CH3:45])=[O:29]

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 2723695Leucine methyl ester hydrochlorideHCID 59776234HCID 59776234, compound

Product 1

HCID 88377736HCID 88377736, compoundYield 99.9%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

8.68 g of dicyclohexylcarbodiimide was added to 200 ml of a solution of 8.73 g of 3-(3-indolyl)-2-hydroxyiminopropionic acid and 4.83 g of N-hydroxysuccinimide in anhydrous dioxane, with ice-cooling. The mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered to remove the insoluble materials, to obtain a brown solution. Separately, 5.6 ml of triethylamine was added to 70 ml of a suspension of 7.27 g of methyl L-leucinate hydrochloride in anhydrous dioxane. The mixture was stirred at room temperature for 2 hours. Thereto was added the above brown solution. The mixture was stirred for 16 hours. The reaction mixture was diluted with 700 ml of ethyl acetate. The resulting solution was washed with 1N hydrochloric acid, an aqueous solution saturated with sodium chloride and an aqueous solution saturated with sodium hydrogen carbonate in this order, then dried with anhydrous magnesium sulfate, and subjected to distillation to remove the solvent, to obtain 13.81 g of methyl N-[2-hydroxyimino-3-(3-indolyl)propionyl]-L-leucinate as a brown oily substance.

Workup

  1. temperaturecooling
  2. filtrationThe reaction mixture was filtered
  3. customto remove the insoluble materials
  4. customto obtain a brown solution
  5. stirringThe mixture was stirred at room temperature for 2 hours
  6. additionThereto was added the above brown solution
  7. stirringThe mixture was stirred for 16 hours
  8. washThe resulting solution was washed with 1N hydrochloric acid
  9. dry with materialan aqueous solution saturated with sodium chloride and an aqueous solution saturated with sodium hydrogen carbonate in this order, then dried with anhydrous magnesium sulfate
  10. distillationsubjected to distillation
  11. customto remove the solvent

Sources & evidence

ORD record
ord-dfb36c420a89474c90c9c52b06bd85c8
Source dataset
uspto-grants-1997_03
Patent number
US05607934

Reaction notes

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