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Acetic Acid → C29H28ClNO2

HRID 342011
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HRID 342011 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H:20]([OH:33])[CH2:21][CH2:22][C:23]4[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=4C(OC)=O)[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:34][Mg+].[Br-].[CH3:37][C:38]([OH:40])=O>C1(C)C=CC=CC=1.C1(C)C=CC=CC=1.C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H:20]([OH:33])[CH2:21][CH2:22][C:23]4[CH:24]=[CH:29][CH:30]=[CH:31][C:32]=4[C:38]([OH:40])([CH3:37])[CH3:34])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 540063032-[3-(S)-[3-(2-(7-Chloro-2-quinolinyl)(E/Z)ethenyl)phenyl]-3-hydroxypropyl]benzoic acid methyl esterHCID 178418689HCID 178418689, 화합물

생성물 1

HCID 54563620C29H28ClNO2

시약·촉매·용매 2

HCID 1140Toluene용매HCID 22635083
Tetrahydrofuran toluene
용매

실험 절차

To a solution of the hydroxyester of Step 2 (38.68 g, 84.36 mmol) in 600 mL of toluene at 0° C. was added slowly 225 mL of 1.5M MeMgBr in toluene:THF 3:1 and the mixture was stirred at r.t. for 4 h. It was then poured into 2 L cold 12% NH4OAc and 25 mL of AcOH were added. The products were extracted in EtOAc, washed with brine, dried over Na2SO4 and concentrated. Flash chromatography of the residue with EtOAc:toluene 15:85 and 25:75 afforded first the methyl ketone derivative, then the title compound. Yield 24.06 g, 62%.

후처리

  1. additionwere added
  2. extractionThe products were extracted in EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customFlash chromatography of the residue with EtOAc:toluene 15:85 and 25:75 afforded first the methyl ketone derivative

출처 및 근거

ORD 기록
ord-aad9cda2c6c943af90fbee9df5b5fe79
출처 데이터셋
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05856322

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