Tetrabutylammonium Fluoride → HCID 21875586, compound

HRID 2077706Notes

Reaction equation

HRID 2077706 reaction equation
[Si]([O:8][C:9]1[CH:41]=[CH:40][C:12]2[N:13]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH:26][C:27]([NH:29][S:30]([C:33]4[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=4)(=[O:32])=[O:31])=[O:28])=[CH:20][CH:19]=3)[C:14]([CH2:16][CH3:17])=[N:15][C:11]=2[CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:16]([C:14]1[N:13]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH:26][C:27]([NH:29][S:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)(=[O:32])=[O:31])=[O:28])=[CH:20][CH:19]=2)[C:12]2[CH:40]=[CH:41][C:9]([OH:8])=[CH:10][C:11]=2[N:15]=1)[CH3:17]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67098924HCID 67098924, compound

Product 1

HCID 21875586HCID 21875586, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-{[tert-butyl(dimethyl)silyl]oxy}-2-ethyl-1-(4-{2-[({[(4-methylphenyl)sulfonyl]amino}carbonyl)amino]ethyl}phenyl)-1H-benzimidazole (step 5, 78 mg, 0.13 mmol) in THF (5 mL) was added tetrabutylammonium fluoride (1.0 M solution in THF, 0.16 mL, 0.16 mmol) at 0° C. The mixture was stirred at 0° C. for 2.5 h, then concentrated. The residue was dissolved in water (30 mL) and extracted with dichloromethane (50 mL). The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane/methanol (gradient elution from 20:1 to 10:1) to afford 57 mg (92%) of the title compound as white amorphous: MS (ESI) m/z 479 (M+H)+; 1H-NMR (DMSO-d6) δ 7.76 (2H, d, J=7.6 Hz), 7.35-7.39 (6H, m), 6.96 (1H, s), 6.85 (1H, d, J=8.6 Hz), 6.65 (1H, d, J=8.6 Hz), 6.51 (1H, br.s), 3.17 (2H, br.s), 2.76 (2H, t, 6.6 Hz), 2.67 (2H, q, J=7.6 Hz), 2.34 (3H, s), 1.20 (3H, t, J=7.6 Hz).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in water (30 mL)
  3. extractionextracted with dichloromethane (50 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel eluting with dichloromethane/methanol (gradient elution from 20:1 to 10:1)

Sources & evidence

ORD record
ord-c68598e9c01d45328dcda6201f3f0d3c
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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