Triethylsilane → HCID 18538706, compound

HRID 412949Notes

Reaction equation

HRID 412949 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([C:38](=O)[CH:39]([CH3:41])[CH3:40])=[CH:34][CH:33]=3)[CH2:27][CH2:26]2)[C:10]([CH:12]2[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([CH2:38][CH:39]([CH3:41])[CH3:40])=[CH:34][CH:33]=3)[CH2:27][CH2:26]2)[C:10]([CH:12]2[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 18539212HCID 18539212, compound

Product 1

HCID 18538706HCID 18538706, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of the title compound of example 335 (318 mg, 0.50 mmol) in trifluoroacetic acid (5 mL) was added triethylsilane (0.399 mL, 2.50 mmol),and the mixture was stirred at room temperature for 2 days. The reaction mixture was evaporated under reduced pressure, 1N aqueous sodium hydroxide (15 mL) was added and the aqueous layer was extracted with ethyl acetate (15 mL, 2×10 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was subjected to column chromatography (silica gel 10 g, ethyl acetate/methanol=1/0 to 9/1). The fractions containing the product were collected and evaporated under reduced pressure. Diisopropyl ether was added to the residue, the resulting precipitate was collected by filtration, washed with diisopropyl ether and dried under reduced pressure to afford the title compound (236 mg, 0.38 mmol, yield 76%) as a white solid.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure, 1N aqueous sodium hydroxide (15 mL)
  2. additionwas added
  3. extractionthe aqueous layer was extracted with ethyl acetate (15 mL, 2×10 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. additionThe fractions containing the product
  8. customwere collected
  9. customevaporated under reduced pressure
  10. additionDiisopropyl ether was added to the residue
  11. filtrationthe resulting precipitate was collected by filtration
  12. washwashed with diisopropyl ether
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-edc69bd97bfb483585438c0f9e3c3fe5
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

Loading…