Dicyclohexylcarbodiimide → HCID 54191163, compound

HRID 1982506Notes

Reaction equation

HRID 1982506 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.O.[C:17]([O:21][C:22]([NH:24][C@H:25]([C:30]([OH:32])=O)[CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23])([CH3:20])([CH3:19])[CH3:18].ON1C(=O)CCC1=O.[N:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1>C(OCC)(=O)C>[CH3:29][CH:27]([CH3:28])[CH2:26][C@H:25]([NH:24][C:22](=[O:23])[O:21][C:17]([CH3:18])([CH3:19])[CH3:20])[C:30]([N:50]1[CH2:51][CH2:52][N:47]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][N:41]=2)[CH2:48][CH2:49]1)=[O:32]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 944591-(2-Pyridyl)piperazineHCID 12373896N-Boc-L-Leucine Hydrate

Product 1

HCID 54191163HCID 54191163, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Under cooling with ice, an ethyl acetate solution (40 ml) of N,N'-dicyclohexylcarbodiimide (10.3 g) was added dropwise to an ethyl acetate solution (150 ml) containing tert-butoxycarbonyl-L-leucine monohydrate (12.5 g) and N-hydroxy succinimide (5.76 g), and the mixture was stirred at room temperature for 3 hours. While cooling again with ice, 1-(2-pyridyl)piperazine (8.16 g) was added, and the mixture was stirred overnight at room temperature. The precipitate was removed by filtration, and the filtrate was washed first with an aqueous sodium carbonate solution and then with a saturated sodium chloride solution, dried over sodium sulfate and distilled under reduced pressure to remove the solvent, whereupon a crude reaction mixture was obtained. The reaction mixture was purified by silica gel column chromatography (developing solvent:methylene chloride:methanol=10:1) to yield 16.1 g of tert-butyl (s)-3-methyl-1-[4-(2-pyridyl)piperazine-1-yl carbonyl]butylcarbamate (yield: 85.6%).

Workup

  1. temperatureUnder cooling with ice
  2. additionwas added
  3. stirringthe mixture was stirred overnight at room temperature
  4. customThe precipitate was removed by filtration
  5. washthe filtrate was washed first with an aqueous sodium carbonate solution
  6. dry with materialwith a saturated sodium chloride solution, dried over sodium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customwhereupon a crude reaction mixture
  10. customwas obtained
  11. customThe reaction mixture was purified by silica gel column chromatography (developing solvent:methylene chloride:methanol=10:1)

Sources & evidence

ORD record
ord-ccb19550f00c4ca093f89a34bc3d7dee
Source dataset
uspto-grants-1986_06
Patent number
US04596803

Reaction notes

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