4-Phenylbutyric Acid → HCID 13176955, compound

HRID 371436Notes

Reaction equation

HRID 371436 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[C:38]([C:43](=[NH:45])[NH2:44])[CH:39]=2)[CH:34]=1)(=O)=O>N1C=CC=CC=1>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([O:12][C:33]2[CH:42]=[CH:41][C:40]3[C:35](=[CH:36][CH:37]=[C:38]([C:43](=[NH:44])[NH2:45])[CH:39]=3)[CH:34]=2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 47754-Phenylbutyric AcidHCID 10868DicyclohexylcarbodiimideHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

Product 1

HCID 13176955HCID 13176955, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2.9 g of 4-phenylbutyric 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 and the mixture was stirred for 24 hours at room temperature and removed of insolubles. Ethyl ether was added to the filtrate and the precipitate was collected by filtration. The precipitate was recrystallized from a DMF-ethyl ether mixture to obtain 2.3 g of a white powder of 6-amidino-2-naphthyl 4-phenylbutyrate methanesulfonate.

Workup

  1. stirringthe mixture was stirred for 24 hours at room temperature
  2. customremoved of insolubles
  3. additionEthyl ether was added to the filtrate
  4. filtrationthe precipitate was collected by filtration
  5. customThe precipitate was recrystallized from a DMF-ethyl ether mixture

Sources & evidence

ORD record
ord-1aecc3ed18e54b7ab6dba2c458a98f53
Source dataset
uspto-grants-1985_07
Patent number
US04532255

Reaction notes

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