Dicyclohexylcarbodiimide → HCID 178512132, compound

HRID 1154579Notes

Reaction equation

HRID 1154579 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([OH:21])=[O:20])[CH2:15][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:42]1[CH:47]=[CH:46][C:45]([CH:48]=[CH:49][C:50](=[NH:52])[NH2:51])=[CH:44][CH:43]=1)(=O)=O>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([O:21][C:42]2[CH:47]=[CH:46][C:45]([CH:48]=[CH:49][C:50](=[NH:51])[NH2:52])=[CH:44][CH:43]=2)=[O:20])[CH2:15][CH2:14]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 54417104HCID 54417104, compoundHCID 178523389HCID 178523389, compound

Product 1

HCID 178512132HCID 178512132, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5.0 g of trans-4-benzyloxycarbonylaminomethylcyclohexanecarboxylic acid in 50 ml of dried pyridine, while being cooled in ice, was added 4.2 g of DCC. After 30 minutes of stirring, to the mixture was added 4.4 g of 4-(β-amidinoethenyl)phenol methanesulfonate. The mixture was stirred overnight at room temperature. The DCU precipitated from the reaction mixture was separated by filtration and washed with pyridine. Ethyl ether was added to the combined filtrate to precipitate a white substance which was collected by filtration, washed with ethyl ether, and recrystallized from ethanol to yield 5.7 g of colorless needle crystals of 4-(β-amidinoethenyl)pnenyl trans-4-benzyloxycarbonylaminomethylcyclohexanecarboxylate methanesulfonate.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customThe DCU precipitated from the reaction mixture
  3. customwas separated by filtration
  4. washwashed with pyridine
  5. additionEthyl ether was added to the combined filtrate
  6. customto precipitate a white substance which
  7. filtrationwas collected by filtration
  8. washwashed with ethyl ether
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-c75e7b4dc30b41838228de3f2421fa46
Source dataset
uspto-grants-1984_12
Patent number
US04490388

Reaction notes

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