Potassium Carbonate → HCID 86604885, compound

HRID 2219891Notes

Reaction equation

HRID 2219891 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:14][C:15]#[C:16][Si](C)(C)C)[CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:14][C:15]#[CH:16])[CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 14115006HCID 14115006, compound

Product 1

HCID 86604885HCID 86604885, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-4-Methyl-N-(5-(trimethylsilyl)pent-4-yn-2-yl)benzenesulfonamide (2.0 g, 6.5 mmol) was dissolved in 15 mL MeOH and treated with K2CO3 (1.3 g, 9.7 mmol). The resulting mixture was stirred for 2 h at RT. The reaction mixture was quenched with sat. NH4Cl and the solvent removed. The residue was partitioned between EtOAc/H2O. The organic layer was washed with sat. NaHCO3, H2O, brine, dried over MgSO4 and concentrated. The residue was purified using SiO2 (80% hexanes: 20% acetone) to afford the title compound. MS (m/z): 238.3 (M+H) (Calc'd for C12H15NO2S: 237.32).

Workup

  1. customThe reaction mixture was quenched with sat. NH4Cl
  2. customthe solvent removed
  3. customThe residue was partitioned between EtOAc/H2O
  4. washThe organic layer was washed with sat. NaHCO3, H2O, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-adbd605cb68a4aeda6b4157427a42349
Source dataset
uspto-grants-2008_08
Patent number
US07414134B2

Reaction notes

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