Acetic acid, (p-(1-pyrrolyl)phenyl)- → HCID 67900358, compound

HRID 979232Notes

Reaction equation

HRID 979232 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:28]([O:30][C:31](=[O:43])[CH:32]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=1)[CH2:33][CH3:34])[CH3:29]>C1COCC1>[CH2:28]([O:30][C:31](=[O:43])[CH:32]([CH2:35][C:36]1[CH:37]=[CH:38][C:39]([NH:42][C:13](=[O:15])[CH2:12][C:9]2[CH:8]=[CH:7][C:6]([N:1]3[CH:2]=[CH:3][CH:4]=[CH:5]3)=[CH:11][CH:10]=2)=[CH:40][CH:41]=1)[CH2:33][CH3:34])[CH3:29]

Participants

5

Reactant 3

HCID 30923Acetic acid, (p-(1-pyrrolyl)phenyl)-HCID 682631,1'-CarbonyldiimidazoleHCID 20201859HCID 20201859, compound

Product 1

HCID 67900358HCID 67900358, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4-(1-pyrryl)phenylacetic acid (3 g) in anhydrous THF (50 ml) is additioned with a solution of carbonyldiimidazole (2.9 g) in THF (80 ml). After 45 minutes a solution of ethyl-2-(p-aminobenzyl)-butyrate (3.3 g) in THF (30 ml). is added. It is reflux heated for an hour, then dried and the residue is dissolved in dichloromethane. The organic solution is washed, first with NaOH 1M, then with HCl 1M and lastly with water. After drying on anhydrous sodium sulfate it is filtered and dried. A yellow solid (1.4 g) is obtained which melts at 100°-102° C. Analysis:

Workup

  1. additionis added
  2. temperatureIt is reflux
  3. temperatureheated for an hour
  4. customdried
  5. dissolutionthe residue is dissolved in dichloromethane
  6. washThe organic solution is washed, first with NaOH 1M
  7. dry with materialAfter drying on anhydrous sodium sulfate it
  8. filtrationis filtered
  9. customdried

Sources & evidence

ORD record
ord-716151ebdee34149b64692f5c3635f33
Source dataset
uspto-grants-1987_05
Patent number
US04666936

Reaction notes

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