Potassium tert-butoxide → HCID 178429794, compound

HRID 2219885Notes

Reaction equation

HRID 2219885 reaction equation
FC(F)(F)C1C=C(S(O[CH2:13][C@@H:14]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)(=[O:19])=[O:18])[CH3:15])(=O)=O)C=CC=1.CC([O-])(C)C.[K+]>C1COCC1>[CH3:13][CH:14]1[CH2:15][N@@:16]1[S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86604884HCID 86604884, compound

Product 1

HCID 178429794HCID 178429794, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-2-(3-(Trifluoromethyl)benzenesulfonamido)propyl 3-(trifluoromethyl)benzene-sulfonate (1.60 g, 3.26 mmol) was dissolved in 25 mL dry THF and treated with KOtBu (5.0 g, 4.9 mmol). The resulting mixture was stirred for 20 h at RT. Thee reaction mixture was quenched with sat. NH4Cl and the solvent was removed. The residue was partitioned between EtOAc/H2O. The organic layer was washed with sat. NH4Cl, H2O, brine, dried over MgSO4 and concentrated. The residue was purified by SiO2 (90% hexanes: 10% Acetone) to afford the final compound. MS (m/z): 266.1 (M+H) (Calc'd for C10H10F3NO2S: 265.25).

Workup

  1. customThee reaction mixture was quenched with sat. NH4Cl
  2. customthe solvent was removed
  3. customThe residue was partitioned between EtOAc/H2O
  4. washThe organic layer was washed with sat. NH4Cl, H2O, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by SiO2 (90% hexanes: 10% Acetone)

Sources & evidence

ORD record
ord-9e7c8973b571451e8cd13c9191613c04
Source dataset
uspto-grants-2008_08
Patent number
US07414134B2

Reaction notes

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