1-Naphthaleneacetic Acid → 2-Benzyl-3-(1-naphthylacetamido)propionic acid ethyl ester

HRID 1607392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1607392
[C:1]1([CH2:11][C:12]([OH:14])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:27]([O:29][C:30](=[O:41])[CH:31]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:32][NH2:33])[CH3:28]>ClCCl>[CH2:27]([O:29][C:30](=[O:41])[CH:31]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:32][NH:33][C:12](=[O:14])[CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH3:28]

Komponenten

5

Edukt 3

HCID 68621-Naphthaleneacetic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 19611763Ethyl 3-amino-2-benzylpropanoate

Produkt 1

HCID 543933582-Benzyl-3-(1-naphthylacetamido)propionic acid ethyl esterAusbeute 41,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 173 g of 1-naphthylacetic acid and 151 mg of 1,1'-carbonyldiimidazole in dry dichloromethane was stirred for 1 hour at room temperature. To the mixture was added 227 mg of 3-amino-2-benzylpropionic acid ethyl ester obtained, and the mixture was heated under reflux for 16 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate, and then the organic layer was washed successively with a 1N-hydrochloric acid, a 5% aqueous sodium bicarbonate solution and water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative silica gel thin layer chromatography (developing solvent: chloroform/ethanol=5/1 by volume) to obtain 169 mg of 2-benzyl-3-(1-naphthylacetamido)propionic acid ethyl ester as colorless crystals.

Aufarbeitung

  1. customobtained
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 16 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washthe organic layer was washed successively with a 1N-hydrochloric acid
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by preparative silica gel thin layer chromatography (developing solvent: chloroform/ethanol=5/1 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-a0a54804f39f45f09862ffb0276b7a54
Quelldatensatz
uspto-grants-1989_09
Patentnummer
US04863904

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