Water → (+/-)-2-(1-Naphthylmethylcarbamoyl)-3-phenylpropionic acid

HRID 1607390Notes

Reaction equation

HRID 1607390 reaction equation
[C:1]1([CH2:11][NH:12][C:13](=[O:24])[CH:14]([C:22]#N)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-:25].[Na+].[OH2:27]>C(O)C>[C:1]1([CH2:11][NH:12][C:13]([CH:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]([OH:27])=[O:25])=[O:24])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 19851387N-(1-naphthylmethyl)-2-cyano-3-phenylpropionamide

Product 1

HCID 14600096(+/-)-2-(1-Naphthylmethylcarbamoyl)-3-phenylpropionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a mixture of 1 ml of ethanol and 2 ml of water were dissolved 123 mg of the amide obtained and 0.66 g of sodium hydroxide, and the solution was heated under reflux for 16 hours. After removal of ethanol, the residue was washed with diethyl ether, and then adjusted to a pH of 2 by adding a 2N-hydrochloric acid. The solution was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 103 mg of (±)-2-(1-naphthylmethylcarbamoyl)-3-phenylpropionic acid as colorless crystals.

Workup

  1. customobtained
  2. temperatureunder reflux for 16 hours
  3. customAfter removal of ethanol
  4. washthe residue was washed with diethyl ether
  5. additionby adding a 2N-hydrochloric acid
  6. extractionThe solution was extracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fdf308f4593b4e058f78455f0781283b
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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