Chlorotrimethylsilane → HCID 58513582, compound

HRID 241642Notes

Reaction equation

HRID 241642 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH2:17][CH:18]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]4)(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:3][CH2:2]1.Cl[Si](C)(C)C>CO>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH2:17][CH:18]4[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]4)(=[O:15])=[O:16])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 58513612HCID 58513612, compound

Product 1

HCID 58513582HCID 58513582, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-((1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)methyl)piperidine-1-carboxylate (STEP C, 1.39 g, 2.76 mmol) in methanol (15 mL) was added chlorotrimethylsilane (1.41 mL, 11.0 mmol). After stirring for 18 h, the mixture was concentrated in vacuo. The residue was diluted ethyl acetate and basified with saturated sodium bicarbonate aqueous solution. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate and concentrated to give the title compound (809 mg, 73%) as an amorphous.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0c7f29696d6746699616570ad2d84300
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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