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Sodium → HCID 59558650, Verbindung

HRID 1175155
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1175155
[Na].CO[C:4]([C:6]1([CH2:17][NH:18][C:19](=[O:26])[CH2:20][C:21]([O:23][CH2:24]C)=[O:22])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)=[O:5]>CO.C1(C)C=CC=CC=1>[CH3:24][O:23][C:21]([CH:20]1[C:4](=[O:5])[C:6]2([CH2:9][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:7]2)[CH2:17][NH:18][C:19]1=[O:26])=[O:22]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 5360545SodiumHCID 59558653HCID 59558653, Verbindung

Produkt 1

HCID 59558650HCID 59558650, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Sodium metal (870 mg; 38 mmol) is dissolved in methanol (55 ml) and combined with a solution of 3-[(2-ethoxycarbonyl-acetylamino)-methyl]-azetidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester in toluene (165 ml). The reaction mixture is heated to 90° C. for 1 hour, cooled to 7-9° C. and the precipitated white crystals (Na-salt of title compound) filtered off. The crystals are dissolved in water, acidified by the addition of 2N HCl and extracted with CH2Cl2 three times. The combined organic phases are dried over Na2SO4, filtered, evaporated and yield the title compound as white crystals (5.6 g; 48%). A second crop of the title compound is obtained by evaporating the above toluene/methanol filtrate to almost dryness, taking up the resin in 2N HCl and extracting with CH2Cl2 three times. The combined organic phases are dried over Na2SO4, filtered, evaporated and yielded the second crop of title compound as brownish solid (3.22 g; 27%).

Aufarbeitung

  1. temperaturecooled to 7-9° C.
  2. filtrationthe precipitated white crystals (Na-salt of title compound) filtered off
  3. dissolutionThe crystals are dissolved in water
  4. additionacidified by the addition of 2N HCl
  5. extractionextracted with CH2Cl2 three times
  6. dry with materialThe combined organic phases are dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-894021dc7ff44eb482b4fe964441c6a3
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07838674B2

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