Water → HCID 66939221, compound

HRID 1257376Notes

Reaction equation

HRID 1257376 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[S:5][C:6]=1[CH2:7][N:8]1[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[CH:10]=[N:9]1.[OH-].[Na+].O>C(O)C.O1CCCC1>[CH3:1][C:2]1[N:3]=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=2)[S:5][C:6]=1[CH2:7][N:8]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[N:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 66939566HCID 66939566, compound

Product 1

HCID 66939221HCID 66939221, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a mixed solution of the compound (70 mg, 0.18 mmol) obtained in Example 70c in ethanol/tetrahydrofuran (v/v=1/1, 4 mL) was added 2N aqueous sodium hydroxide solution (0.71 mL, 1.4 mmol), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the aqueous layer was washed with diethyl ether, neutralized with 1N aqueous hydrochloric acid solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was recrystallized (ethyl acetate-hexane) to give the title compound (44 mg, 67%) as colorless crystals.

Workup

  1. washthe aqueous layer was washed with diethyl ether
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe resulting crude title compound was recrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-3f588e5e83a84d9fa0800d9868f7850f
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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