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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
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인쇄 미리보기

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HRID 1739659 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8848c292411e43e9a2670a1589e76449
출처 데이터셋
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05968875

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