Piperidine → 3-{3-[4-(2-Carboxy-ethyl)-3-methyl-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indol-5-yl}-propionic acid

HRID 1937564Notes

Reaction equation

HRID 1937564 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[C:7]([CH3:13])=[C:8]([CH:11]=O)[NH:9][CH:10]=1)([OH:3])=[O:2].[C:14]([CH2:17][CH2:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:28])[CH2:22]2)([OH:16])=[O:15].N1CCCCC1>C(O)C>[C:1]([CH2:4][CH2:5][C:6]1[C:7]([CH3:13])=[C:8]([CH:11]=[C:22]2[C:21]3[C:25](=[CH:26][CH:27]=[C:19]([CH2:18][CH2:17][C:14]([OH:16])=[O:15])[CH:20]=3)[NH:24][C:23]2=[O:28])[NH:9][CH:10]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 151607523-(5-formyl-4-methyl-1H-pyrrol-3-yl)propanoic acidHCID 219257025-(2-Carboxyethyl)-2-oxindole

Product 1

HCID 690343773-{3-[4-(2-Carboxy-ethyl)-3-methyl-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indol-5-yl}-propionic acidYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2-Carboxyethyl)-2-formyl-3-methylpyrrole (90.6 mg), 102.6 mg 5-carboxyethyl-2-oxindole and 75 μL piperidine in 2 mL of ethanol were heated at 95° C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven overnight. The crude solid was purified by chromatography a silica gel column eluting with ethyl acetate-hexane-acetic acid to give 121 mg (66%) of the title compound as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. filtrationThe precipitate was filtered
  4. washwashed with water to pH 6
  5. customdried in a vacuum oven overnight
  6. customThe crude solid was purified by chromatography a silica gel column
  7. washeluting with ethyl acetate-hexane-acetic acid

Sources & evidence

ORD record
ord-f6e616ff0c3f445084975533e8690969
Source dataset
uspto-grants-2002_05
Patent number
US06395734B1

Reaction notes

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