Water → Methyl 2-(4-methoxybenzamido)acetate

HRID 58868

Reaktionsgleichung

Reaktionsgleichung von HRID 58868
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1.[CH3:18][O:19][C:20](=[O:23])[CH2:21][NH2:22].O>C1COCC1>[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH:22][CH2:21][C:20]([O:19][CH3:18])=[O:23])=[O:14])=[CH:11][CH:10]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7477p-Anisoyl chlorideHCID 11430Potassium CarbonateHCID 69221Glycine methyl ester

Produkt 1

HCID 523508Methyl 2-(4-methoxybenzamido)acetateAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Saturated aqueous potassium carbonate (190 mL) and 4-methoxybenzoyl chloride (60.8 g, 358 mmol) were added to a solution of glycine methyl ester (30.0 g, 239 mmol) in THF (100 mL) at 0° C. The reaction mixture was stirred for 3 h at 0° C. and then poured into water (100 mL). The resulting mixture was extracted with EtOAc (200 ml×2). The combined extracts were dried over anhydrous sodium sulfate and concentrated to afford methyl 2-(4-methoxybenzamido)acetate (46.2 g, 86% yield) as a colorless solid, which was used directly without further purification.

Aufarbeitung

  1. extractionThe resulting mixture was extracted with EtOAc (200 ml×2)
  2. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b0d37ab5c48848208e067ceb6c2abc65
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434761B2

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