Acetonitrile → HCID 68175846, compound

HRID 1477873Notes

Reaction equation

HRID 1477873 reaction equation
[C:1](#[N:3])[CH3:2].[Li]CCCC.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:22]2[C:30]3[C:25](=[C:26]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23]2)([CH2:20][CH3:21])[C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=1>C1COCC1>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:22]2[C:30]3[C:25](=[C:26]([NH:31][S:32]([CH3:35])(=[O:33])=[O:34])[CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23]2)([CH2:20][CH3:21])[C:17]([OH:19])([CH3:18])[CH2:2][C:1]#[N:3])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 70560671HCID 70560671, compoundHCID 178418339Butyllithium

Product 1

HCID 68175846HCID 68175846, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of acetonitrile (244 mg, 5.94 mmol) in THF (20 mL) was added n-BuLi (2.6 mL, 6.5 mmol, 2.5 M in hexane) dropwise at −78° C. After stirring for 0.5 h, a solution of the product from Step A (480 mg, 1.19 mmol) in THF (5 mL) was added to the mixture at −78° C. The resulting mixture was stirred at −78° C. for 0.5 h, and then quenched with saturated ammonium chloride solution, extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with PE/EA (15/1 to 4/1, v/v) to afford the title compound as a colorless amorphous solid. LC/MS m/z=468.0 [M+Na]+.

Workup

  1. stirringThe resulting mixture was stirred at −78° C. for 0.5 h
  2. customquenched with saturated ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with PE/EA (15/1 to 4/1

Sources & evidence

ORD record
ord-21f2c3593b624e3ea2a2deb8e0d7049d
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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