1H-Indole-3-propanoic acid → HCID 54385026, compound

HRID 1975391Notes

Reaction equation

HRID 1975391 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:2]1.[CH3:15][NH:16][C:17]1[CH:18]=[C:19]([C:23]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)=[CH:24][CH2:25][CH2:26][CH2:27][C:28]([O:30]C)=[O:29])[CH:20]=[CH:21][CH:22]=1.C(N1C=CN=C1)(N1C=CN=C1)=O>O1CCCC1>[CH3:15][N:16]([C:12](=[O:14])[CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[C:17]1[CH:18]=[C:19]([C:23]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)=[CH:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 37441H-Indole-3-propanoic acidHCID 682631,1'-CarbonyldiimidazoleHCID 54467159HCID 54467159, compound

Product 1

HCID 54385026HCID 54385026, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.9 g of 3-(3-indolyl)-propionic acid, 2.3 g of methyl 6-(3-methylaminophenyl)-6-(3-pyridyl)-hex-5-enoate and 1.8 g of carbonyldiimidazole is refluxed for 48 hours in 50 ml of tetrahydrofuran. The reaction mixture is evaporated down, the residue is taken up in water and extracted with ethyl acetate. The organic phase is evaporated down and the residue is saponified in a mixture of 20 ml of ethanol and 6 ml of 4N sodium hydroxide solution at 50° C. for 30 minutes. The reaction mixture is neutralised by the addition of citric acid and extracted with ethyl acetate. The organic phase is concentrated by evaporation and the residue is recrystallised from ethyl acetate/diisopropylether.

Workup

  1. customThe reaction mixture is evaporated down
  2. extractionextracted with ethyl acetate
  3. customThe organic phase is evaporated down
  4. additionthe residue is saponified in a mixture of 20 ml of ethanol and 6 ml of 4N sodium hydroxide solution at 50° C. for 30 minutes
  5. additionThe reaction mixture is neutralised by the addition of citric acid
  6. extractionextracted with ethyl acetate
  7. concentrationThe organic phase is concentrated by evaporation
  8. customthe residue is recrystallised from ethyl acetate/diisopropylether

Sources & evidence

ORD record
ord-36ac6ca8de12415d8e12fbf120ca0c54
Source dataset
uspto-grants-1994_02
Patent number
US05286736

Reaction notes

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