Acetone → HCID 11501747, compound

HRID 643718Notes

Reaction equation

HRID 643718 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 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-5-(methylsulfonyl)-1H-benzimidazole (Step D, 8.22 g, 25.7 mmol) in tetrahydrofuran (200 mL) was added lithium bis(trimethylsilyl)amide (1.07 M in hexane, 28.8 mL, 30.8 mmol) at −40° C. under nitrogen atmosphere. After stirring for 10 min, acetone (20 mL) 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 water (200 mL) and extracted with ethyl acetate (300 mL×3). The combined organic layers were dried over sodium sulfate and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2 as eluent) to afford the title compound (4.68 g, 48%) as a white solid.

Workup

  1. stirringAfter stirring for 18 h
  2. customthe mixture was quenched with water (200 mL)
  3. extractionextracted with ethyl acetate (300 mL×3)
  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 column chromatography on silica gel (hexane:ethyl acetate=3:2 as eluent)

Sources & evidence

ORD record
ord-05a63cfdb4804e2caa7aea3cf188089a
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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