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Sodium Hydroxide → Ethyl 2-[3-(aminomethyl)-1-azetidinyl]-4-methyl-5-thiazolecarboxylate

HRID 43912
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 43912
Br.C(O)(=O)C.C(OC([NH:16][CH2:17][CH:18]1[CH2:21][N:20]([C:22]2[S:23][C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:25]([CH3:27])[N:26]=2)[CH2:19]1)=O)C1C=CC=CC=1.[OH-].[Na+]>C(O)(=O)C>[NH2:16][CH2:17][CH:18]1[CH2:21][N:20]([C:22]2[S:23][C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:25]([CH3:27])[N:26]=2)[CH2:19]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 67549285HCID 67549285, Verbindung

Produkt 1

HCID 67549202Ethyl 2-[3-(aminomethyl)-1-azetidinyl]-4-methyl-5-thiazolecarboxylateAusbeute 60,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A 30% hydrogen bromide/acetic acid solution (0.64 mL, 3.29 mmol) was added to a solution of ethyl 2-[3-({[(benzyloxy)carbonyl]amino}methyl)azetidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (233b) (128 mg, 0.33 mmol) in acetic acid (1 mL), and the mixture was stirred at room temperature for 100 minutes. A 1 N aqueous sodium hydroxide solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. Thereafter, the filtrate was concentrated under reduced pressure to obtain 51 mg of the title compound as a colorless oily substance (61%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThereafter, the filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1cdfad84d9434ffdb649ae79574d1476
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08536197B2

Notizen zur Reaktion

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