Acetonitrile → HCID 57524147, compound

HRID 1477877Notes

Reaction equation

HRID 1477877 reaction equation
[C:1](#[N:3])[CH3:2].[Li]CCCC.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:23]2[C:31]3[C:26](=[C:27]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)([CH2:21][CH3:22])[C:17](OC)=[O:18])=[CH:12][CH:11]=1>O1CCCC1>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:23]2[C:31]3[C:26](=[C:27]([NH:32][S:33]([CH3:36])(=[O:34])=[O:35])[CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)([CH2:21][CH3:22])[C:17](=[O:18])[CH2:2][C:1]#[N:3])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 57524786HCID 57524786, compoundHCID 178418339Butyllithium

Product 1

HCID 57524147HCID 57524147, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of acetonitrile (180 mg, 4.4 mmol) in tetrahydrofuran (3 mL) was added BuLi (1.9 mL, 4.8 mmol, 2.5 M in hexane) at −78° C. After stirring for 30 min, a solution of methyl 2-(4-chlorophenyl)-2-(4-(methylsulfonamido)-1H-indol-1-yl)butanoate (840 mg, 2.0 mmol, Enantiomer A), as described in Example 3 step D, in tetrahydrofuran (3 mL) was added to the mixture at −78° C. The resulting mixture was stirred at −78° C. for another 1 h, and then quenched with water (15 mL), extracted with ethyl acetate. The combined organics were washed with brine (15 mL), dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography eluting with PE/EA (5/1 to 3/1, v/v) to get the title compound as a colorless amorphous solid (Enantiomer A). LC/MS m/z=429.8[M+H]+.

Workup

  1. additionwas added to the mixture at −78° C
  2. stirringThe resulting mixture was stirred at −78° C. for another 1 h
  3. customquenched with water (15 mL)
  4. extractionextracted with ethyl acetate
  5. washThe combined organics were washed with brine (15 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel chromatography
  10. washeluting with PE/EA (5/1 to 3/1

Sources & evidence

ORD record
ord-18e69ad8c9da4a87b9d2cc9a6f8040ea
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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