Boron trifluoride etherate → HCID 22624680, compound

HRID 279356Notes

Reaction equation

HRID 279356 reaction equation
O[C:2]1([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)[CH2:7][CH2:6][CH:5]([CH:8]([CH3:17])[CH2:9][NH:10][S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[CH2:4][CH2:3]1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>ClCCl>[S:19]1[CH:20]=[CH:21][CH:22]=[C:18]1[CH:2]1[CH2:7][CH2:6][CH:5]([CH:8]([CH3:17])[CH2:9][NH:10][S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 9819577HCID 9819577, compound

Product 1

HCID 22624680HCID 22624680, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 80 mg (0.23 mmol) of the material prepared in Example 1 in 2 ml of dichloromethane and 32 mg (0.28 mmol) of triethylsilane at −78° C., was added 49 mg (0.35 mmol) of boron trifluoride diethyl etherate. The mixture was stirred for 1 h., the bath was removed and stirred at ambient temperature for 30 min. A saturated solution of sodium bicarbonate (2 ml) was added and extracted with dichloromethane, dried over Na2SO4, filtered and concentrated in vacuo. Chromatography (75 g of silica gel, 25% ethyl acetate/hexane) of the residue afforded 38 mg (50%) of the title compound. Analysis calculated for C16H27NO2S2: %C, 58.32; %H, 8.26; %N, 4.25. Found: %C, 59.06; %H, 8.48; %N, 4.31. Field Desorption Mass Spectrum: M=329.

Workup

  1. customthe bath was removed
  2. stirringstirred at ambient temperature for 30 min
  3. additionA saturated solution of sodium bicarbonate (2 ml) was added
  4. extractionextracted with dichloromethane
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5dce70c4c8264223b1167c21db3760d1
Source dataset
uspto-grants-2002_03
Patent number
US06362230B1

Reaction notes

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