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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
ノート
印刷プレビュー

反応式

HRID 1739659 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8848c292411e43e9a2670a1589e76449
出典データセット
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05968875

反応ノート

読み込み中…

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