Water → HCID 15859214, compound

HRID 2378363Notes

Reaction equation

HRID 2378363 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14].[H-].[Na+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[N:12]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[S:13]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 54300325HCID 54300325, compound

Product 1

HCID 15859214HCID 15859214, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.00 g (2.86 mmol) of the product of Example 28 in 10 mL of DMF was added 0.14 g (3.57 mmol) of 60% sodium hydride. The resulting mixture was stirred for 30 min at room temperature and then 0.42 mL (3.57 mmol) of benzyl bromide was added. This reaction mixture was stirred overnight at room temperature, poured into water and then extracted with ether. The combined organics were washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo to provide a white solid which was recrystallized from ethyl acetate (EtOAc)/Hexanes to provide 1.084 g (85%) of the desired product as a white solid. Electrospray Mass Spec: m/z 428.3 (M+H)+.

Workup

  1. stirringThis reaction mixture was stirred overnight at room temperature
  2. extractionextracted with ether
  3. washThe combined organics were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide a white solid which
  8. customwas recrystallized from ethyl acetate (EtOAc)/Hexanes

Sources & evidence

ORD record
ord-10f20380cab14640b17390ce65c8fa12
Source dataset
uspto-grants-2008_12
Patent number
US07470794B2

Reaction notes

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