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Sodium Methoxide → HCID 66701012, Verbindung

HRID 2062079
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2062079
C(O[C:4](=[O:13])[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[SH:12])C.C[O-].[Na+].[CH3:17][O:18][C:19](=[O:28])[C:20]([NH:23][C:24](=[O:27])[CH2:25]Cl)([CH3:22])[CH3:21]>CO>[CH3:17][O:18][C:19](=[O:28])[C:20]([NH:23][C:24]([C:25]1[S:12][C:6]2[CH:7]=[CH:8][C:9]([F:11])=[CH:10][C:5]=2[C:4]=1[OH:13])=[O:27])([CH3:22])[CH3:21]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10942334Sodium MethoxideHCID 16217758Ethyl 5-fluoro-2-sulfanylbenzoateHCID 43700001HCID 43700001, Verbindung

Produkt 1

HCID 66701012HCID 66701012, VerbindungAusbeute 70,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1.00 g 5-fluoro-2-mercaptobenzoic acid ethyl ester in 10 ml methanol 0.81 g of sodium methoxide were added portionwise, followed by addition of 0.97 g 2-(2-chloro-acetylamino)-2-methyl-propionic acid methyl ester. After refluxing the reaction under argon-atmosphere for 0.5 h the resulting mixture was filtrated, 20 ml water and 1.25 ml of acetic acid were added and the precipitated product was collected by filtration, washed with water, dissolved in ethyl acetate and THF, dried over sodium sulphate, filtrated and concentrated in vacuo. The resulting crude product was crystallized from diethylether to yield 1.10 g 2-[(5-fluoro-3-hydroxy-benzo[b]thio-phene-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester.

Aufarbeitung

  1. temperatureAfter refluxing
  2. customthe reaction under argon-atmosphere for 0.5 h the resulting mixture
  3. filtrationwas filtrated
  4. addition20 ml water and 1.25 ml of acetic acid were added
  5. filtrationthe precipitated product was collected by filtration
  6. washwashed with water
  7. dissolutiondissolved in ethyl acetate
  8. dry with materialTHF, dried over sodium sulphate
  9. filtrationfiltrated
  10. concentrationconcentrated in vacuo
  11. customThe resulting crude product was crystallized from diethylether

Quellen und Nachweise

ORD-Eintrag
ord-a79b41356cf04122be7460093b5b2929
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08283479B2

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