Sodium Hydroxide → HCID 66670195, compound

HRID 1514651Notes

Reaction equation

HRID 1514651 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:8]([CH3:19])=[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:6]=1[CH2:25][OH:26])([CH3:4])([CH3:3])[CH3:2].Cl.O1CCO[CH2:30][CH2:29]1.[OH-].[Na+]>C(O)C>[C:1]([C:5]1[N:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:8]([CH3:19])=[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:6]=1[CH2:25][O:26][CH2:29][CH3:30])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 204431481,4-Dioxane hydrochlorideHCID 66670254HCID 66670254, compound

Product 1

HCID 66670195HCID 66670195, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A 719 mg portion of ethyl 5-tert-butyl-1-[2-(4-fluorophenyl)ethyl]-4-(hydroxymethyl)-2-methyl-1H-pyrrole-3-carboxylate was suspended in 10 ml of ethanol, and 2.0 ml of 4 M hydrogen chloride/1,4-dioxane was added, followed by stirring overnight at room temperature. By adding 10 ml of a 1 M sodium hydroxide aqueous solution, ethanol was evaporated under a reduced pressure. After extraction with ethyl acetate, the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After evaporation of the solvent under a reduced pressure, the residue was purified by silica gel column chromatography (Chromatorex (registered trademark), ethyl acetate:hexane=1:30-1:20-1:15) to obtain 623 mg of ethyl 5-tert-butyl-4-(ethoxymethyl)-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxylate as a colorless oil.

Workup

  1. customwas evaporated under a reduced pressure
  2. extractionAfter extraction with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter evaporation of the solvent under a reduced pressure
  6. customthe residue was purified by silica gel column chromatography (Chromatorex (registered trademark), ethyl acetate:hexane=1:30-1:20-1:15)

Sources & evidence

ORD record
ord-b0f622ac487e43d79e7ddfca8307db82
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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