Tetrabutylammonium Fluoride → HCID 57709084, compound

HRID 546979Notes

Reaction equation

HRID 546979 reaction equation
C([O:3][C:4](=[O:44])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH2:41][CH3:42])([C:21]3[CH:26]=[CH:25][C:24]([C:27]#[C:28][C:29]4([O:35][Si](C)(C)C)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)=[C:23]([CH3:40])[CH:22]=3)[CH2:19][CH3:20])=[CH:14][C:13]=2[CH3:43])=[CH:10][CH:11]=1)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:19]([C:18]([C:15]1[CH:16]=[CH:17][C:12]([C:9]2[N:8]=[CH:7][C:6]([CH2:5][C:4]([OH:44])=[O:3])=[CH:11][CH:10]=2)=[C:13]([CH3:43])[CH:14]=1)([C:21]1[CH:26]=[CH:25][C:24]([C:27]#[C:28][C:29]2([OH:35])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[C:23]([CH3:40])[CH:22]=1)[CH2:41][CH3:42])[CH3:20]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57709161HCID 57709161, compound

Product 1

HCID 57709084HCID 57709084, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[6-(4-{1-Ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclohexylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic acid ethyl ester (Example 98-(1); 14 mg, 0.023 mmol) was dissolved in tetrahydrofuran (0.2 mL). Tetra-n-butylammonium fluoride (1 M solution in tetrahydrofuran; 0.1 mL) was added, and the mixture was stirred at room temperature for three hours. The reaction mixture was concentrated under reduced pressure, and then the residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=1/1). The product was dissolved in methanol/tetrahydrofuran=1/1 (1 mL). A 1 N sodium hydroxide aqueous solution (0.1 mL) was added, and the mixture was stirred at room temperature for one hour. A 30% sodium dihydrogenphosphate aqueous solution (0.3 mL) was added to the reaction mixture, and then the reaction mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/ethyl acetate=1/1) to give the title compound (3 mg, 25%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=1/1)
  3. dissolutionThe product was dissolved in methanol/tetrahydrofuran=1/1 (1 mL)
  4. additionA 1 N sodium hydroxide aqueous solution (0.1 mL) was added
  5. stirringthe mixture was stirred at room temperature for one hour
  6. additionA 30% sodium dihydrogenphosphate aqueous solution (0.3 mL) was added to the reaction mixture
  7. concentrationthe reaction mixture was concentrated under reduced pressure
  8. customThe residue was purified by preparative TLC (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-7a8c3472cd8d498ebc2fcd9cd79ae84e
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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