Chlorotrimethylsilane → HCID 58513578, compound

HRID 241669Notes

Reaction equation

HRID 241669 reaction equation
[CH3:1][N:2]([CH3:33])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([CH:17]3[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[CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30].Cl[Si](C)(C)C>CO>[NH:19]1[CH2:20][CH:17]([S:14]([C:12]2[CH:11]=[CH:10][C:9]3[N:5]([CH2:4][CH2:3][N:2]([CH3:33])[CH3:1])[C:6]([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[N:7][C:8]=3[CH:13]=2)(=[O:15])=[O:16])[CH2:18]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 58513581HCID 58513581, compound

Product 1

HCID 58513578HCID 58513578, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 3-(1-(2-(dimethylamino)ethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)azetidine-1-carboxylate (prepared in STEP F of Example 1, 327 mg, 0.683 mmol) in methanol (4 mL) was added chlorotrimethylsilane (873 microL, 6.80 mmol). After stirring for 20 h at room temperature, the mixture was concentrated in vacuo. The residue was diluted with methanol (10 mL) and filtered through SCX column. The column was washed with 1 mol/L ammonia in methanol solution to wash out the product. The filtrated was concentrated to give the title compound (270 mg, 97%) as an oil.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionThe residue was diluted with methanol (10 mL)
  3. filtrationfiltered through SCX column
  4. washThe column was washed with 1 mol/L ammonia in methanol solution
  5. washto wash out the product
  6. concentrationThe filtrated was concentrated

Sources & evidence

ORD record
ord-16c6056e9f8f4bba8961fa0984a1d36b
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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