Acetic Acid → C29H28ClNO2

HRID 342011Notes

Reaction equation

HRID 342011 reaction equation
[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

Participants

6

Reactant 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, compound

Product 1

HCID 54563620C29H28ClNO2

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-aad9cda2c6c943af90fbee9df5b5fe79
Source dataset
uspto-grants-1999_01
Patent number
US05856322

Reaction notes

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