Carbon Dioxide → HCID 72189887, compound

HRID 1487044Notes

Reaction equation

HRID 1487044 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:4][C:3]=1[S:16]([N:19]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=1[CH3:31])[CH2:20][CH:21]([CH3:23])[CH3:22])(=[O:18])=[O:17].[Li]CCCC.[C:37](=[O:39])=[O:38]>O1CCCC1>[CH3:31][C:25]1[CH:26]=[C:27]([CH3:30])[CH:28]=[CH:29][C:24]=1[N:19]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:16]([C:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:7][C:2]=1[C:37]([OH:39])=[O:38])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 72193575HCID 72193575, compoundHCID 178418339Butyllithium

Product 1

HCID 72189887HCID 72189887, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 2-bromo-N-(2,4-dimethylphenyl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide (50 mg, 0.098 mmol) in tetrahydrofuran (THF) at −78° C. was added nBuLi 1.6 M in hexanes (92 μL, 0.147 mmol) and the reaction stirred for 1 hour. After this time carbon dioxide (small pellet) was added and the reaction mixture stirred at −78° C. for 30 minutes, then warmed to 20° C. and stirred for a further 1 hour. The reaction was quenched with saturated ammonium chloride solution and the mixture concentrated in vacuo. The residue was then taken up in ethyl acetate (20 mL) and the organic phase was washed with saturated ammonium chloride solution (2×25 mL), the organics were dried using a hydrophobic frit and evaporated in vacuo to give the crude product as a colourless gum, 40 mg. LCMS [LCMS2] Rt 0.97 min, m/z (ES+) 476 (M+H).

Workup

  1. stirringthe reaction mixture stirred at −78° C. for 30 minutes
  2. stirringstirred for a further 1 hour
  3. customThe reaction was quenched with saturated ammonium chloride solution
  4. concentrationthe mixture concentrated in vacuo
  5. washthe organic phase was washed with saturated ammonium chloride solution (2×25 mL)
  6. customthe organics were dried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-4f73bdc5e18c4393a09b44b380cfd7cb
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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