Water → HCID 14706434, compound

HRID 731025Notes

Reaction equation

HRID 731025 reaction equation
[Si]([O:8][C@@H:9]([CH3:26])[C@:10]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[F:25])([OH:17])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[F:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[C@:10]([OH:17])([C@@H:9]([OH:8])[CH3:26])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 67175826HCID 67175826, compound

Product 1

HCID 14706434HCID 14706434, compoundYield 868.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.10 g of (2R,3S)-3-(tert-butyldimethylsilyloxy)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol in 1 mL of THF was added 0.3 mL of TBAF (1 M) at room temperature. Stirring was performed at room temperature for 3.5 hours, and 5 mL of water was added thereto. Then, extraction was performed with ethyl acetate (30 mL). After drying over anhydrous sodium sulfate, concentration was performed under reduced pressure to obtain a crude product. The resulting product was purified by column on silica gel to obtain 0.61 g of the title compound (yield: 87%). 1H-NMR (400 MHz, CDCl3) δ: 0.97 (d, 3H, J=6.3 Hz), 4.31 (q, 1H, J=6.3 Hz), 4.79-4.82 (m, 2H), 6.67-6.81 (m, 2H), 7.32-7.38 (m, 1H), 7.72 (s, 1H), 7.93 (s, 1H).

Workup

  1. extractionThen, extraction
  2. dry with materialAfter drying over anhydrous sodium sulfate, concentration
  3. customto obtain a crude product
  4. customThe resulting product was purified by column on silica gel

Sources & evidence

ORD record
ord-c97e0c9222b148258c6336f37729997a
Source dataset
uspto-grants-2009_09
Patent number
US07582781B2

Reaction notes

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