Chlorotrimethylsilane → HCID 58513609, compound

HRID 241666Notes

Reaction equation

HRID 241666 reaction equation
[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([C@H:17]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]3)(=[O:16])=[O:15])=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31].Cl[Si](C)(C)C>CO>[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([C@H:17]3[CH2:21][CH2:20][NH:19][CH2:18]3)(=[O:15])=[O:16])=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:29][C:30]([CH3:32])([CH3:31])[CH3:33]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 58513588HCID 58513588, compound

Product 1

HCID 58513609HCID 58513609, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (S)-tert-butyl 3-(1-(2-(dimethylamino)ethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)pyrrolidine-1-carboxylate (STEP E, 980 mg, 1.99 mmol) in methanol (6 mL) was added chlorotrimethylsilane (1.27 mL, 9.95 mmol). The mixture was stirred at 50° C. for 16 h. The resulting mixture was concentrated. The residue was added 2 mol/L sodium hydroxide aqueous solution to pH>7 and the mixture was extracted with ethyl acetate (150 mL). The organic layer was washed with brine and dried over sodium sulfate. The resulting solution was concentrated to give the title compound (776 mg, 99%) as an oil.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. additionThe residue was added 2 mol/L sodium hydroxide aqueous solution to pH>7
  3. extractionthe mixture was extracted with ethyl acetate (150 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationThe resulting solution was concentrated

Sources & evidence

ORD record
ord-7a66d6a31ed2453daa24a113d9b5d024
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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