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Sodium Chloride → (2S, 4S)-1-(2-hydroxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

HRID 5114
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 5114
I[CH2:2][CH2:3][OH:4].C(=O)(O)[O-].[Na+].[CH3:10][O:11][C:12]1[CH:28]=[CH:27][C:15]([CH2:16][S:17][C@@H:18]2[CH2:22][NH:21][C@H:20]([C:23](=[O:26])[NH:24][CH3:25])[CH2:19]2)=[CH:14][CH:13]=1.[Cl-].[Na+]>CN(C)C=O>[OH:4][CH2:3][CH2:2][N:21]1[CH2:22][C@@H:18]([S:17][CH2:16][C:15]2[CH:27]=[CH:28][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)[CH2:19][C@H:20]1[C:23](=[O:26])[NH:24][CH3:25]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 12225IodoethanolHCID 516892Sodium BicarbonateHCID 14880277(2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

Produkt 1

HCID 14880306(2S, 4S)-1-(2-hydroxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

934 μl of 2-iodoethanol and 1.01 g of sodium bicarbonate were added, whilst ice-cooling, to a solution of 2.80 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 18 ml of dry dimethylformamide, and the mixture was stirred at 40° C. for 24 hours. At the end of this time, the reaction mixture was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel (eluted with a 15:1 by volume mixture of ethyl acetate and methanol), to afford 2.22 g of the title compound as colorless crystals, melting at 88°-89.5° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was then removed by distillation under reduced pressure
  5. customthe residue was purified by column chromatography through silica gel (
  6. washeluted with a 15:1 by volume mixture of ethyl acetate and methanol),

Quellen und Nachweise

ORD-Eintrag
ord-c4d3c967ee794540a87c6456700647c8
Quelldatensatz
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05242914

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