Tetrabutylammonium Fluoride → HCID 69322440, compound

HRID 448087Notes

Reaction equation

HRID 448087 reaction equation
[CH2:1]([N:5]1[C:9]([CH3:10])=[C:8]([C:11]([O:17][Si](C)(C)C)([CH3:16])[C:12]([F:15])([F:14])[F:13])[S:7]/[C:6]/1=[CH:22]\[C:23]([C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1[O:32][CH3:33])=[O:24])[CH2:2][CH2:3][CH3:4].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([N:5]1[C:9]([CH3:10])=[C:8]([C:11]([OH:17])([CH3:16])[C:12]([F:15])([F:14])[F:13])[S:7]/[C:6]/1=[CH:22]\[C:23]([C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1[O:32][CH3:33])=[O:24])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69322495HCID 69322495, compound

Product 1

HCID 69322440HCID 69322440, compoundYield 889.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 123A (80 mg, 0.015 mmol) in THF at 0° C. was treated with TBAF (0.015 mmol) and stirred for 1 hr. The reaction mixture was partitioned between EtOAc and brine, dried (MgSO4), concentrated and the residue was purified by flash chromatography eluting with 0-100% EtoAc in hexane to give 60 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.96 (t, J=7.3 Hz, 3 H), 1.33-1.49 (m, 2 H), 1.66 (d, J=7.1 Hz, 2 H), 1.74 (s, 3 H), 2.41 (s, 3 H), 3.86 (s, 3 H), 3.90-4.01 (m, 2 H), 6.57 (s, 1 H), 7.05 (s, 1 H), 7.12 (d, J=8.8 Hz, 1 H), 7.42 (dd, J=8.8, 2.7 Hz, 1 H), 7.64 (d, J=3.1 Hz, 1 H). MS (DCI), m/z 450 (M+H)+. Anal calcd for C20H23ClF3NO3S: C, 53.39; H, 5.15; N, 3.11. Found: C, 53.20; H, 5.01; N, 2.89.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customthe residue was purified by flash chromatography
  5. washeluting with 0-100% EtoAc in hexane

Sources & evidence

ORD record
ord-c99e195edcd3427180ff23ec4607063c
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

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