Acetone → HCID 11501747, compound

HRID 1817892Notes

Reaction equation

HRID 1817892 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:33][C:34]([CH3:36])=[O:35]>O1CCCC1>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH2:17][C:34]([CH3:36])([OH:35])[CH3:33])(=[O:15])=[O:16])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 2733832Lithium HexamethyldisilazideHCID 11587800HCID 11587800, compound

Product 1

HCID 11501747HCID 11501747, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-5-(methylsulfonyl)-1H-benzimidazole (Example 4, 67 mg, 0.21 mmol) in tetrahydrofuran was added lithium bis(trimethylsilyl)amide (1.06 M in hexane, 217 μL, 0.23 mmol) at −40° C. under nitrogen atmosphere. After stirring for 5 min, excess acetone was added at −40° C. and the mixture was allowed to warm to room temperature. After stirring for 18 h, the mixture was quenched with saturated ammonium chloride aqueous solution and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. The filtrate was concentrated and the residue was purified by PTLC (hexane:ethyl acetate=1:1, three times) to afford the title compound (6.4 mg, 8%) as a white amorphous solid.

Workup

  1. stirringAfter stirring for 18 h
  2. customthe mixture was quenched with saturated ammonium chloride aqueous solution
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by PTLC (hexane:ethyl acetate=1:1, three times)

Sources & evidence

ORD record
ord-1453d186b87e4abb9cdc7f42a697be31
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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