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Methanol → 4'-[3-[Hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid

HRID 1617508
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인쇄 미리보기

반응식

HRID 1617508 반응식
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[CH2:18][C:19](=[N:27][OH:28])[C:20]3[CH:25]=[CH:24][N:23]=[C:22]([CH3:26])[CH:21]=3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=[O:4].CO.[OH-].[Li+].OS([O-])(=O)=O.[K+]>C1COCC1>[OH:28][N:27]=[C:19]([C:20]1[CH:25]=[CH:24][N:23]=[C:22]([CH3:26])[CH:21]=1)[CH2:18][CH:17]([C:14]1[CH:13]=[CH:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=2)=[CH:16][CH:15]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH3:35]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 1363599834'-[3-[Hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid methyl ester

생성물 1

HCID 1363599844'-[3-[Hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of 4′-[3-[hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid methyl ester (352 mg) in THF (7.5 mL) was added a drop of methanol and a 1 M aqueous lithium hydroxide solution (7.6 mL) at 0° C. The reaction mixture was stirred at rt for 2 hours. A 1M aqueous solution of KHSO4 (7.5 mL) was added, the phases were separated and an extraction was made with EtOAc and a saturated solution of NH4Cl. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH 9:1) to yield 4′-[3-[hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid as a mixture of E and Z isomers (3:1) as a white foam (288 mg, 84%), MS (ESI−): m/z=449.2 ([M−H]−).

후처리

  1. customat 0° C
  2. customthe phases were separated
  3. extractionan extraction
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH 9:1)

출처 및 근거

ORD 기록
ord-cbc1636fd40a4cd1b61ede6020d052f1
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08765730B2

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