Diethyl Ether → HCID 13146250, compound

HRID 2413218Notes

Reaction equation

HRID 2413218 reaction equation
[CH:1]1([CH2:6][C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH:3]=[CH:2]1.C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[C:35]([C:40](=[NH:42])[NH2:41])[CH:36]=2)[CH:31]=1)(=O)=O.C(OCC)C>N1C=CC=CC=1>[CH:1]1([CH2:6][C:7]([O:9][C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[C:35]([C:40](=[NH:41])[NH2:42])[CH:36]=3)[CH:31]=2)=[O:8])[CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10868DicyclohexylcarbodiimideHCID 962162-Cyclopentene-1-acetic acidHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13146250HCID 13146250, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2.2 g of 2-cyclopentene-1-acetic acid in 50 ml of anhydrous pyridine, while being cooled in ice and stirred, was added 4.4 g of DCC. After 30 minutes, 5.0 g of 6-amidino-2-naphthol methanesulfonate was added to the mixture and stirred for 24 hours at room temperature. The precipitate formed by the addition of ethyl ether was collected by filtration, admixed with dimethylformamide, and filtered to remove the insolubles. Ethyl ether was added to the filtrate and the precipitate which was formed was collected by filtration and recrystallized from a dimethyl formamide-ethyl ether mixture to yield 2.1 g of a white powder of 6-amidino-2-naphthyl 2-cyclopenteneacetate methanesulfonate.

Workup

  1. stirringstirred for 24 hours at room temperature
  2. filtrationwas collected by filtration
  3. filtrationfiltered
  4. customto remove the insolubles
  5. additionEthyl ether was added to the filtrate
  6. customthe precipitate which was formed
  7. filtrationwas collected by filtration
  8. customrecrystallized from a dimethyl formamide-ethyl ether mixture

Sources & evidence

ORD record
ord-342852dee9584b53af3cfe2ef4a38a26
Source dataset
uspto-grants-1985_01
Patent number
US04496584

Reaction notes

Loading…