2-(1-Naphthylmethylene)-3-(phenethylcarbamoyl)propionic acid → HCID 13746611, compound

HRID 1905312Notes

Reaction equation

HRID 1905312 reaction equation
[C:1]1([CH:11]=[C:12]([CH2:16][C:17](=[O:27])[NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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(O)(=O)C.[Pd]>[C:1]1([CH2:11][CH:12]([CH2:16][C:17](=[O:27])[NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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 1

HCID 540395402-(1-Naphthylmethylene)-3-(phenethylcarbamoyl)propionic acid

Product 1

HCID 13746611HCID 13746611, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 4.00 g of 2-(1-naphthylmethylene)-3-(phenethylcarbamoyl)propionic acid in 120 ml of acetic acid was hydrogenated over 2.0 g of a 10% palladium-charcoal under a hydrogen atmosphere at room temperature. After filtration of the catalyst, the filtrate was evaporated under reduced pressure, and hexane was added to the residue. The precipitated crystals were collected by filtration to obtain 3.40 g of (±)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)-propionic acid as colorless crystals.

Workup

  1. filtrationAfter filtration of the catalyst
  2. customthe filtrate was evaporated under reduced pressure, and hexane
  3. additionwas added to the residue
  4. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-84898cb865724536a6346d8d4d438e29
Source dataset
uspto-grants-1989_06
Patent number
US04841067

Reaction notes

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