Tetrahydrofuran → 2-(benzyloxy)-N-(5-cyano-2-fluoro-3-hydroxy-6-methylbiphenyl-4-yl)acetamide

HRID 17346Notes

Reaction equation

HRID 17346 reaction equation
[CH2:1]([O:8][CH2:9][C:10](Cl)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[NH2:18][C:19]1[C:26]([OH:27])=[C:25]([F:28])[C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:23]([CH3:35])[C:20]=1[C:21]#[N:22].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][C:10]([NH:18][C:19]1[C:26]([OH:27])=[C:25]([F:28])[C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:23]([CH3:35])[C:20]=1[C:21]#[N:22])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 177085Benzyloxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 860974464-Amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl

Product 1

HCID 866308382-(benzyloxy)-N-(5-cyano-2-fluoro-3-hydroxy-6-methylbiphenyl-4-yl)acetamideYield 77.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under nitrogen atmosphere, benzyloxyacetyl chloride (489 μl, 3.10 mmol) was dropwise added to a tetrahydrofuran solution (10 ml) of 2-amino-5-phenyl-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-41) (500 mg, 2.06 mmol) and sodium hydrogencarbonate (520 mg, 6.19 mmol) cooled with ice, followed by stirring at room temperature for 18 hours. Ethyl acetate was added to the reaction liquid, followed by washing with water and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was recrystallized and purified with n-hexane/ethyl acetate to obtain the entitled compound (621 mg, 1.59 mmol, 77%) as a white solid.

Workup

  1. temperaturecooled with ice
  2. washby washing with water and saturated brine
  3. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customThe resulting residue was recrystallized
  6. custompurified with n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-f3c7c2d7056b4b81b49efd7fc92c0797
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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