Dicyclohexylcarbodiimide → HCID 13146256, compound

HRID 2413221Notes

Reaction equation

HRID 2413221 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:40]1[CH:49]=[CH:48][C:47]2[C:42](=[CH:43][CH:44]=[C:45]([C:50](=[NH:52])[NH2:51])[CH:46]=2)[CH:41]=1)(=O)=O>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][C:40]1[CH:49]=[CH:48][C:47]2[C:42](=[CH:43][CH:44]=[C:45]([C:50](=[NH:51])[NH2:52])[CH:46]=2)[CH:41]=1)=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acidHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13146256HCID 13146256, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4.7 g of ε-benzyloxycarbonylaminocaproic acid in 50 ml of anhydrous pyridine, while being cooled in ice, was added 4.4 g of DCC. After stirring for 30 minutes, 5.0 g of 6-amidino-2-naphthol methanesulfonate was added to the mixture and stirred overnight at room temperature. The precipitate was separated by filtration and washed with a small volume of pyridine. The filtrate and the washings were added to stirred ethyl ether. The precipitated crystals were collected by filtration, recrystallized from an ethanol-ether mixture, and washed with acetone to obtain 6.2 g of white crystals of 6-amidino-2-naphthyl ε-benzyloxycarbonylaminocaproate methanesulfonate.

Workup

  1. stirringstirred overnight at room temperature
  2. customThe precipitate was separated by filtration
  3. washwashed with a small volume of pyridine
  4. additionThe filtrate and the washings were added
  5. stirringto stirred ethyl ether
  6. filtrationThe precipitated crystals were collected by filtration
  7. customrecrystallized from an ethanol-ether mixture
  8. washwashed with acetone

Sources & evidence

ORD record
ord-a7abff4a68d3400a9efca54e64cf6264
Source dataset
uspto-grants-1985_01
Patent number
US04496584

Reaction notes

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