Water → HCID 59831915, compound

HRID 268904Notes

Reaction equation

HRID 268904 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][CH:6]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.O.[OH-].[K+]>C(O)C>[NH:18]1[C:19]2[C:15](=[CH:14][C:13]([CH:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:5][C:4]([OH:22])=[O:3])=[CH:21][CH:20]=2)[CH:16]=[CH:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 59831884HCID 59831884, compound

Product 1

HCID 59831915HCID 59831915, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(1H-indol-5-yl)-3-phenyl-propionic acid ethyl ester CCLXXIII (0.48 g, 1.6 mmol) in ethanol (30 mL) was added water (ca. 5 mL) followed by potassium hydroxide in pellets (ca. 0.6 g) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was evaporated under reduced pressure to remove the organic solvent and the residue was diluted with water (50 mL) and diethyl ether (50 mL). The resulting mixture was acidified by addition of an aqueous solution of hydrochloric acid (1 M) and was extracted twice with diethyl ether (50 mL). The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure to afford 0.42 g (98% yield) of 3-(1H-indol-5-yl)-3-phenyl-propionic acid CCLXXIV as a yellow solid without further purifications.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customto remove the organic solvent
  3. additionthe residue was diluted with water (50 mL) and diethyl ether (50 mL)
  4. additionThe resulting mixture was acidified by addition of an aqueous solution of hydrochloric acid (1 M)
  5. extractionwas extracted twice with diethyl ether (50 mL)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9f7464e6290b4d5786390d76be008fb2
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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