Tetrabutylammonium Fluoride → HCID 69468859, compound

HRID 853785Notes

Reaction equation

HRID 853785 reaction equation
C([Si](C)(C)[O:6][C:7]1([CH:10]2[N:15]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:14]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH2:13][CH2:12][CH2:11]2)[CH2:9][CH2:8]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([S:16]([N:15]2[CH:10]([C:7]3([OH:6])[CH2:9][CH2:8]3)[CH2:11][CH2:12][CH2:13][CH:14]2[C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)(=[O:18])=[O:17])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69472239HCID 69472239, compound

Product 1

HCID 69468859HCID 69468859, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the silyl ether of Step 6 (79.2 mg, 1.56 mmol) in THF (20 mL) was treated with TBAF (2.0 mmol, 2.0 mL, 1M in THF). After stirring for 2 h at room temperature, the solvent was removed and the residue was purified by chromatography (eluting with EtOAc) to give 54.4 mg (89%) of the title compound as a white solid. 1H NMR (CDCl3 300 MHz) δ8.75 (1H, s) 8.50 (1H, s), 8.12 (1H, d), 7.80 (2H, d), 7.50 (2H, d), 7.35 (1H, m), 5.18 (1H, m), 3.60 (1H, d), 2.23 (1H, m), 1.97 (1H, m), 1.80 (1H, m), 1.48–1.23 (4H, m), 1.10 (1H, m), 0.64–0.45 (3H, m), MS (ES) m/e 393 (M)+.

Workup

  1. customthe solvent was removed
  2. customthe residue was purified by chromatography (eluting with EtOAc)

Sources & evidence

ORD record
ord-7f834f1ac7454a198615a8dd824d51f4
Source dataset
uspto-grants-2007_08
Patent number
US07256186B2

Reaction notes

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