Phenylacetic Acid → HCID 13176927, compound

HRID 371433Notes

Reaction equation

HRID 371433 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[C:36]([C:41](=[NH:43])[NH2:42])[CH:37]=2)[CH:32]=1)(=O)=O.C(OCC)C>N1C=CC=CC=1>[C:1]1([CH2:7][C:8]([O:10][C:31]2[CH:40]=[CH:39][C:38]3[C:33](=[CH:34][CH:35]=[C:36]([C:41](=[NH:42])[NH2:43])[CH:37]=3)[CH:32]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 999Phenylacetic AcidHCID 3283Diethyl EtherHCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13176927HCID 13176927, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2.4 g of phenylacetic acid in 50 ml of anhydrous pyridine, while being cooled and stirred, was added 4.4 g of DCC. After 30 minutes, to the mixture was added 5.0 g of 6-amidino-2-naphthol methanesulfonate. The mixture was stirred at room temperature for 24 hours, mixed with ethyl ether, and the precipitate was collected by filtration. The precipitate was dissolved in DMF and the insolubles were filtered off. The filtrate containing the DMF-soluble substances was mixed with ethyl ether, the resulting precipitate was collected by filtration and recrystallized from a mixture of DMF and ethyl ether to obtain 3.0 g of a white powder of 6-amidino-2-naphthyl phenylacetate methanesulfonate.

Workup

  1. stirringThe mixture was stirred at room temperature for 24 hours
  2. filtrationthe precipitate was collected by filtration
  3. dissolutionThe precipitate was dissolved in DMF
  4. filtrationthe insolubles were filtered off
  5. additionThe filtrate containing the DMF-soluble substances
  6. additionwas mixed with ethyl ether
  7. filtrationthe resulting precipitate was collected by filtration
  8. customrecrystallized from a mixture of DMF and ethyl ether

Sources & evidence

ORD record
ord-5cc8f54b97d5446daae048c5f775b610
Source dataset
uspto-grants-1985_07
Patent number
US04532255

Reaction notes

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