Boron trifluoride etherate → HCID 66817075, compound

HRID 1755059Notes

Reaction equation

HRID 1755059 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH2:16][CH2:17][S:18]([N:21]2[CH2:40][CH2:39][C:24]3([N:28]=[C:27]([CH:29]4[CH2:34][CH2:33][C:32](=[C:35]([CH3:37])[CH3:36])[CH2:31][CH2:30]4)[NH:26][C:25]3=[O:38])[CH2:23][CH2:22]2)(=[O:20])=[O:19])=[C:11]([CH3:41])[CH:10]=1)C)(C)(C)C.B(F)(F)F.CCOCC>ClCCl>[CH3:15][C:13]1[CH:14]=[C:9]([NH:7][CH3:6])[CH:10]=[C:11]([CH3:41])[C:12]=1[CH2:16][CH2:17][S:18]([N:21]1[CH2:22][CH2:23][C:24]2([N:28]=[C:27]([CH:29]3[CH2:34][CH2:33][C:32](=[C:35]([CH3:37])[CH3:36])[CH2:31][CH2:30]3)[NH:26][C:25]2=[O:38])[CH2:39][CH2:40]1)(=[O:19])=[O:20]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 66818060HCID 66818060, compound

Product 1

HCID 66817075HCID 66817075, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 40 4AMS beads were added to a solution of (4-{2-[2-(4-isopropylidene-cyclohexyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3,5-dimethyl-phenyl)-methyl-carbamic acid tert-butyl ester (85.7 mg, 143 μmol) in dichloromethane (1.4 ml), and the mixture was stirred at room temperature for 10 minutes. Thereafter, BF3.Et2O (90.2 μl, 715 μmol) was added to the reaction mixture at 0° C., and the mixture was stirred at room temperature for three hours. The reaction mixture was quenched by adding triethylamine and diluted with ethyl acetate. The organic layer was then washed with a saturated aqueous sodium bicarbonate solution and water, and then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=100/0→92/8) to give 8-[2-(2,6-dimethyl-4-methylamino-phenyl)-ethanesulfonyl]-2-(4-isopropylidene-cyclohexyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (66.0 mg, 92%).

Workup

  1. stirringthe mixture was stirred at room temperature for three hours
  2. customThe reaction mixture was quenched
  3. additionby adding triethylamine
  4. additiondiluted with ethyl acetate
  5. washThe organic layer was then washed with a saturated aqueous sodium bicarbonate solution and water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=100/0→92/8)

Sources & evidence

ORD record
ord-07ca855e93674f0da3ea9a406b96a29c
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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