Tetrabutylammonium Fluoride → HCID 68502983, compound

HRID 1713454Notes

Reaction equation

HRID 1713454 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]([C:15]2([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[N:19]([C:20]3[S:21][C:22]([CH3:25])=[N:23][N:24]=3)[N:18]=[C:17]([C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=3[F:33])[S:16]2)[CH:12]=[CH:13][CH:14]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:33][C:27]1[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:26]=1[C:17]1[S:16][C:15]([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=2)[N:19]([C:20]2[S:21][C:22]([CH3:25])=[N:23][N:24]=2)[N:18]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68505210HCID 68505210, compound

Product 1

HCID 68502983HCID 68502983, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

t-Butyl 3-(2-(3-(tert-butyldimethylsilyloxy)phenyl)-5-(2,5-difluorophenyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1,3,4-thiadiazol-2-yl)propylcarbamate (75 mg, 0.113 mmol) was weighed into a 25 mL flask and dissolved in 10.0 mL of THF, then cooled to 0° C. TBAF (0.39 mL, 0.39 mmol) was added dropwise and the reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was concentrated to dryness, then re-dissolved in DCM, washed with saturated NaHCO3 solution, dried over Na2SO4, and concentrated in vacuo. The residue was purified by removal of tributylamine via successive washes with 1N HCl. The organic layer was concentrated in vacuo, and the yellow oil subject to purification by flash column chromatography (25-60% ethyl acetate/hexanes) to afford the desired product (51 mg, 82% yield) as a yellow foam.

Workup

  1. temperatureto warm to room temperature overnight
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionre-dissolved in DCM
  4. washwashed with saturated NaHCO3 solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by removal of tributylamine via successive washes with 1N HCl
  8. concentrationThe organic layer was concentrated in vacuo
  9. customthe yellow oil subject to purification by flash column chromatography (25-60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-289de08fe84d4625af1f867826dd17a5
Source dataset
uspto-grants-2010_09
Patent number
US07795282B2

Reaction notes

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