Acetic Acid → (+/-)-2-(1-Naphthylmethyl)-3-(phenetylcarbamoyl)propionic acid

HRID 1607395Notes

Reaction equation

HRID 1607395 reaction equation
[C:1]1([CH:11]=[C:12]([CH2:16][C:17](=[O:27])[NH:18]CCC2C=CC=CC=2)[C:13]([OH:15])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:28]([OH:31])(=O)[CH3:29]>[Pd]>[C:1]1([CH2:11][CH:12]([CH2:16][C:17](=[O:27])[NH:18][C:1]2[CH:10]=[CH:5][C:4]([O:31][CH2:28][CH3:29])=[CH:3][CH:2]=2)[C:13]([OH:15])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 540395402-(1-Naphthylmethylene)-3-(phenethylcarbamoyl)propionic acid

Product 1

HCID 86743366(+/-)-2-(1-Naphthylmethyl)-3-(phenetylcarbamoyl)propionic acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 500 mg of 2-(1-naphthylmethylene)-3-(phenethylcarbamoyl)propionic acid in 50 ml of acetic acid was hydrogenated over 250 mg of a 10% palladium/charcoal under a hydrogen atmosphere at room temperature. After filtration of the catalyst, the filtrate was concentrated under reduced pressure, and hexane was added to the residue. The precipitates were collected to obtain 500 mg of (±)-2-(1-naphthylmethyl)-3-(phenetylcarbamoyl)propionic acid as colorless crystals.

Workup

  1. filtrationAfter filtration of the catalyst
  2. concentrationthe filtrate was concentrated under reduced pressure, and hexane
  3. additionwas added to the residue
  4. customThe precipitates were collected

Sources & evidence

ORD record
ord-f8c2972527654e6d900975b17a317c98
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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