3-(4-Aminophenyl)propionic acid → HCID 178434716, compound

HRID 641041Notes

Reaction equation

HRID 641041 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[C:24]([CH3:28])=[N:25][O:26][CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:29].[NH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][C:39]([OH:41])=[O:40])=[CH:33][CH:32]=1>C1COCC1>[CH3:28][C:24]1[C:23]([C:21]([NH:20][C:16]2[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=2)[C:12]([C:8]2[CH:7]=[C:6]3[C:11]([C:3](=[CH:2][NH:30][C:31]4[CH:32]=[CH:33][C:34]([CH2:37][CH2:38][C:39]([OH:41])=[O:40])=[CH:35][CH:36]=4)[C:4](=[O:29])[NH:5]3)=[CH:10][CH:9]=2)=[O:13])=[O:22])=[CH:27][O:26][N:25]=1

Participants

4

Reactant 2

HCID 754513-(4-Aminophenyl)propionic acidHCID 178434718HCID 178434718, compound

Product 1

HCID 178434716HCID 178434716, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 3-Methyl-isoxazole-4-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (prepared below, 100 mg, 0.257 mmol) and THF (2.5 mL). To the resulting solution was added 3-(4-Amino-phenyl)-propionic acid (42.4 mg, 0.257 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and a yellow precipitate formed. The precipitate was filtered then washed with 0° C. iPrOH (˜5 mL) to afford the title compound in 25% yield (0.034 g, 0.0634 mmol).

Workup

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. customa yellow precipitate formed
  4. filtrationThe precipitate was filtered
  5. washthen washed with 0° C. iPrOH (˜5 mL)

Sources & evidence

ORD record
ord-8b510e74d7394a59bd655eeed2f45539
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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