Triethylamine → HCID 12074108, compound

HRID 1061893Notes

Reaction equation

HRID 1061893 reaction equation
[OH:1][C:2]([C:11]1[CH:25]=[CH:24][C:14]2[C:15]3[CH2:16][N:17]([CH3:23])[C:18](=[O:22])[C:19]=3[CH:20]=[CH:21][C:13]=2[CH:12]=1)([C:6]1[N:7]=[CH:8][NH:9][CH:10]=1)[CH:3]([CH3:5])[CH3:4].C(N(CC)CC)C.[CH2:33]([O:36][C:37](Cl)=[O:38])[CH:34]=[CH2:35]>CN(C=O)C.O>[CH2:33]([O:36][C:37]([N:9]1[CH:10]=[C:6]([C:2]([C:11]2[CH:25]=[CH:24][C:14]3[C:15]4[CH2:16][N:17]([CH3:23])[C:18](=[O:22])[C:19]=4[CH:20]=[CH:21][C:13]=3[CH:12]=2)([OH:1])[CH:3]([CH3:5])[CH3:4])[N:7]=[CH:8]1)=[O:38])[CH:34]=[CH2:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 18052Allyl chloroformateHCID 178450030HCID 178450030, compound

Product 1

HCID 12074108HCID 12074108, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

7-[1-Hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one (13.8 g) was suspended in DMF (400 ml) and the mixture was heated to 85° C. to give a homogeneous solution. This solution was cooled in an ice bath and triethylamine (8.6 ml) was added. Then allyloxycarbonyl chloride (5.2 ml) was slowly added and the reaction mixture was stirred at room temperature for 1.5 hrs. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The extracted layers were combined, washed three times with water, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography (carrier: silica gel, developing solvent: dichloromethane-methanol=100:1-40:1) to give the title compound (15.9 g) as colorless crystals.

Workup

  1. customto give a homogeneous solution
  2. temperatureThis solution was cooled in an ice bath
  3. extractionextracted twice with ethyl acetate
  4. washwashed three times with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (carrier: silica gel, developing solvent: dichloromethane-methanol=100:1-40:1)

Sources & evidence

ORD record
ord-f55deb3e979c41e48080a5418e71f664
Source dataset
uspto-grants-2005_11
Patent number
US06960586B2

Reaction notes

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