Tetrabutylammonium Fluoride → HCID 45102606, compound

HRID 1945301Notes

Reaction equation

HRID 1945301 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[F:19][C:20]1[C:21]([C:49]2[CH:54]=[CH:53][C:52]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=3[OH:61])=[CH:51][CH:50]=2)=[CH:22][C:23]2[N:27]=[C:26]([O:28][C:29]3[CH:30]=[CH:31][C:32]([CH3:39])=[C:33]([CH:38]=3)[C:34]([O:36]C)=[O:35])[N:25](COCC[Si](C)(C)C)[C:24]=2[CH:48]=1>C1COCC1>[F:19][C:20]1[C:21]([C:49]2[CH:54]=[CH:53][C:52]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=3[OH:61])=[CH:51][CH:50]=2)=[CH:22][C:23]2[N:27]=[C:26]([O:28][C:29]3[CH:30]=[CH:31][C:32]([CH3:39])=[C:33]([CH:38]=3)[C:34]([OH:36])=[O:35])[NH:25][C:24]=2[CH:48]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68491851HCID 68491851, compound

Product 1

HCID 45102606HCID 45102606, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

TBAF (1 M in THF) (0.63 mL, 0.63 mmol) was added to a solution of methyl 5-[(6-fluoro-5-(2′-hydroxybiphenyl-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate (75 mg, 0.125 mmol) in THF (10 mL). The reaction was heated at 80° C. for 6 h. Volatiles were removed and the residue was purified by HPLC eluting with 20-80% MeCN:water. The resulting white solid was dissolved in MeOH (3 mL) and water (2 mL). Aqueous 5 M NaOH (250 μl) was added. The solution was heated at 70° C. for 30 min. Volatiles were removed and the residue was re-dissolved in 10 mL water and extracted with ethyl acetate to afford the title compound as a white solid product. LC/MS: calculated for C27H19FN2O4 454.45, observed m/e 455(M+H)+ (1.97/4 min). 1H-NMR (500 MHz, D6-acetone): 8.02-6.98 (13H, m), 2.62 (3H, s).

Workup

  1. customVolatiles were removed
  2. customthe residue was purified by HPLC
  3. washeluting with 20-80% MeCN
  4. dissolutionThe resulting white solid was dissolved in MeOH (3 mL)
  5. additionAqueous 5 M NaOH (250 μl) was added
  6. temperatureThe solution was heated at 70° C. for 30 min
  7. customVolatiles were removed
  8. dissolutionthe residue was re-dissolved in 10 mL water
  9. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-ec70ef1d58914db8a73b0a6931eb7482
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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