4-Phenylbutyric Acid → HCID 86739854, compound

HRID 1154582Notes

Reaction equation

HRID 1154582 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.[CH3:28][S:29]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]=[CH:40][C:41](=[NH:43])[NH2:42])=[CH:35][CH:34]=1)(=[O:31])=[O:30]>N1C=CC=CC=1>[CH3:28][S:29]([OH:32])(=[O:31])=[O:30].[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([O:12][C:33]2[CH:38]=[CH:37][C:36]([CH:39]=[CH:40][C:41](=[NH:42])[NH2:43])=[CH:35][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 54417104HCID 54417104, compound

Product 1

HCID 86739854HCID 86739854, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.6 g of 4-phenylbutyric acid in 50 ml of dried pyridine, was added 3.1 g of DCC. After 30 minutes of stirring, 2.6 g of 4-(β-amidinoethenyl)-phenol methanesulfonate was added and the mixture was stirred overnight. The insolubles were removed by filtration and ethyl ether was added to the filtrate to precipitate crystals. The crystals were collected by filtration and recrystallized from ethanol to obtain 2.2 g of 4-(β-amidinoethenyl)phenyl 4-phenylbutyrate methanesulfonate.

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe insolubles were removed by filtration and ethyl ether
  3. additionwas added to the filtrate
  4. customto precipitate crystals
  5. filtrationThe crystals were collected by filtration
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a188c2b6e2ec487f9d7258dccbd820e7
Source dataset
uspto-grants-1984_12
Patent number
US04490388

Reaction notes

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