2-Phenylpropionic acid → HCID 13176929, compound

HRID 371434Notes

Reaction equation

HRID 371434 reaction equation
[CH3:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37]([C:42](=[NH:44])[NH2:43])[CH:38]=2)[CH:33]=1)(=O)=O>N1C=CC=CC=1>[CH3:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([O:5][C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37]([C:42](=[NH:43])[NH2:44])[CH:38]=2)[CH:33]=1)=[O:4]

Participants

5

Reactant 3

HCID 102962-Phenylpropionic acidHCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13176929HCID 13176929, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 50 ml of dried pyridine, were added 3.0 g of α-methylphenylacetic acid and 4.9 g of DCC. The mixture was stirred for 30 minutes under cooling in ice. After adding 5.6 g of 6-amidino-2-naphthol methanesulfonate, while being cooled in ice, the mixture was stirred for one hour, then overnight. The reaction mixture was filtered to collect the precipitate. The precipitate was washed with pyridine and ethyl ether, added to DMF and heated. The insolubles were filtered off and ethyl ether was added to the filtrate to collect the precipitate by filtration. The precipitate was recrystallized from a mixed solvent comprising ethanol and ethyl ether to obtain 1.8 g of a white powder of 6-amidino-2-naphthyl α-methylphenylacetate methanesulfonate.

Workup

  1. temperatureunder cooling in ice
  2. temperaturewhile being cooled in ice
  3. stirringthe mixture was stirred for one hour
  4. customovernight
  5. filtrationThe reaction mixture was filtered
  6. customto collect the precipitate
  7. washThe precipitate was washed with pyridine and ethyl ether
  8. additionadded to DMF
  9. temperatureheated
  10. filtrationThe insolubles were filtered off
  11. additionethyl ether was added to the filtrate
  12. customto collect the precipitate
  13. filtrationby filtration
  14. customThe precipitate was recrystallized from a mixed solvent

Sources & evidence

ORD record
ord-c4c5b2fd14054b788ba3c23612743fab
Source dataset
uspto-grants-1985_07
Patent number
US04532255

Reaction notes

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