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Triethylamine → 2-(1-naphthylmethylene)-3-(N-methyl-N-methoxycarbonylmethylcarbamoyl)propionic acid

HRID 1722903
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1722903
Cl.[CH3:2][O:3][C:4](=[O:8])[CH2:5][NH:6][CH3:7].C(N(CC)CC)C.[C:16]1([CH:26]=[C:27]2[CH2:32][C:31](=[O:33])[O:30][C:28]2=[O:29])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1>ClCCl>[C:16]1([CH:26]=[C:27]([CH2:32][C:31](=[O:33])[N:6]([CH3:7])[CH2:5][C:4]([O:3][CH3:2])=[O:8])[C:28]([OH:30])=[O:29])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 543164283-[(Naphthalen-1-yl)methylidene]oxolane-2,5-dione

Produkt 1

HCID 545054722-(1-naphthylmethylene)-3-(N-methyl-N-methoxycarbonylmethylcarbamoyl)propionic acidAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of 1.40 g of sarcosine methyl ester hydrochloride in 50 ml of dichloromethane were added 1.54 ml of triethylamine and 1.70 g of the 2-(1-naphthylmethylene)succinic anhydride obtained, and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was washed successively, with diluted hydrochloric acid, and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: chloroform) to obtain 2.37 g of 2-(1-naphthylmethylene)-3-(N-methyl-N-methoxycarbonylmethylcarbamoyl)propionic acid as a white powder.

Aufarbeitung

  1. customobtained
  2. washThe reaction mixture was washed successively, with diluted hydrochloric acid
  3. dry with materiala saturated sodium chloride aqueous solution, dried over anhydrous magnesium
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel flash column chromatography (eluent: chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-a272edaa631946dbbd8e74c1389f891e
Quelldatensatz
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04857650

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