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Ethyl Acetate → alpha-(methoxyimino)-N-methyl-2-[[[3-chloro-6-(3-ethyl-3-pentoxycarbonyl)-2-pyridinyl]oxy]methyl]-benzeneacetamide

HRID 1739659
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1739659
[H-].[Na+].[OH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[N:16][O:17][CH3:18])[C:12]([NH:14][CH3:15])=[O:13].[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:27]([OH:29])=[O:28])=[N:24][C:25]=1Cl.C(O[CH2:34][CH3:35])(=O)C>C1COCC1>[CH3:18][O:17][N:16]=[C:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][O:3][C:25]1[C:20]([Cl:19])=[CH:21][CH:22]=[C:23]([C:27]([O:29][C:5]([CH2:34][CH3:35])([CH2:10][CH3:9])[CH2:6][CH3:7])=[O:28])[N:24]=1)[C:12]([NH:14][CH3:15])=[O:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 132780162-Pyridinecarboxylic acid, 5,6-dichloro-HCID 544725602-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

Produkt 1

HCID 131721407alpha-(methoxyimino)-N-methyl-2-[[[3-chloro-6-(3-ethyl-3-pentoxycarbonyl)-2-pyridinyl]oxy]methyl]-benzeneacetamide

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

NaH (60% dispersion in mineral oil, 0.24 g, 6.0 mmol) was added to a solution of 2-hydroxymethyl-α-methyoxyimino-N-methyl-benzeneacetamide (1.11 g, 5.0 mmol) in THF (50 mL). 5,6-Dichloropicolinic acid: 3-ethyl-3-pentyl ester (1.68 g, 5.5 mmol) was dissolved in THF (10 mL) and added slowly via pipet to this mixture. As the mixture was stirred at room temperature under N2 for one hour, the reaction mixture transformed to a dark green solution. The reaction volume was increased to ca. 125 mL with ethyl acetate and washed with water and brine. The organic phase was evaporated in vacuo to provide the crude product which was chromatographed on medium pressure LC using increasing gradient of ethyl acetate in hexane (0-50%). Concentrating chromatographic fractions gave α-(methoxyimino)-N-methyl-2-[[[3-chloro-6-(3-ethyl-3-pentoxycarbonyl)-2-pyridinyl]oxy]methyl]-benzeneacetamide (0.29 g) as a yellow oil.

Aufarbeitung

  1. additionadded slowly via pipet to this mixture
  2. washwashed with water and brine
  3. customThe organic phase was evaporated in vacuo
  4. customto provide the crude product which
  5. customwas chromatographed on medium pressure LC
  6. temperatureusing increasing gradient of ethyl acetate in hexane (0-50%)
  7. concentrationConcentrating chromatographic fractions

Quellen und Nachweise

ORD-Eintrag
ord-8848c292411e43e9a2670a1589e76449
Quelldatensatz
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05968875

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