Diethyl Ether → HCID 178459293, compound

HRID 892126Notes

Reaction equation

HRID 892126 reaction equation
[CH2:1]([C@@H:8]1[CH2:19][N:18]2[C:10]([C:11]3[NH:12][C:13]([CH:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[N:14][C:15]=3[N:16]([CH2:21]C(OC)=O)[C:17]2=[O:20])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][Mg]Br.[Cl-:34].[NH4+].C([O:38][CH2:39][CH3:40])C>O1CCCC1>[ClH:34].[CH2:1]([C@@H:8]1[CH2:19][N:18]2[C:10]([C:11]3[NH:12][C:13]([CH:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[N:14][C:15]=3[N:16]([CH2:21][C:39]([OH:38])([CH3:40])[CH3:31])[C:17]2=[O:20])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 178418573HCID 178418573, compoundHCID 178501545HCID 178501545, compound

Product 1

HCID 178459293HCID 178459293, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 77c (670 mg, 1.65 mmol) obtained in Example 77 was dissolved in tetrahydrofuran (7 mL), to the solution was added methyl magnesium bromide (2.75 mL, a 3.0 mol/L solution in diethyl ether, 5.0 equivalents) under ice cooling, and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture was added saturated aqueous ammonium chloride, and the mixture was warmed to room temperature and stirred for 10 minutes. The reaction mixture was extracted with chloroform, and the resulting organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (chloroform:methanol=99:1). The product was converted into hydrochloride with a 4 mol/L solution of hydrogen chloride in dioxane, and then, after the solvent was evaporated, the product was recrystallized from ethyl acetate to obtain the title compound (460 mg, 68%).

Workup

  1. extractionThe reaction mixture was extracted with chloroform
  2. washthe resulting organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=99:1)
  6. customafter the solvent was evaporated
  7. customthe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ca98771b1f4c4510809b0c7bfd7b4c39
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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