Ammonium Chloride → tert-Butyl 2-oxo-2-(thiophen-3-yl)ethylcarbamate

HRID 2042926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2042926
CON(C)[C:4](=[O:14])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[S:16]1[CH:20]=[CH:19][C:18]([Mg]I)=[CH:17]1.[NH4+].[Cl-]>C1COCC1>[O:14]=[C:4]([C:18]1[CH:19]=[CH:20][S:16][CH:17]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 4428209tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamateHCID 178506590HCID 178506590, Verbindung

Produkt 1

HCID 67995722tert-Butyl 2-oxo-2-(thiophen-3-yl)ethylcarbamateAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the Weinreb amide 45 (1.53 g, 7 mmol) in anhydrous THF (10 mL) was added dropwise (over a 10-min period) a solution of thiophen-3-ylmagnesium iodide (0.3 M in THF, 50 mL) under nitrogen atmosphere at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 18 h. The mixture was poured into a saturated NH4Cl solution and extracted with EtOAc. The organic phase was dried over anhydrous MgSO4, filtered and evaporated under vacuum. The residue was further purified by silica column chromatography to provide the titled compound (776 mg, 46%). MNa+264.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe residue was further purified by silica column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-08bd0cdb854141ca9fb604c79b258954
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586550B2

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