Tetrabutylammonium Fluoride → HCID 178472403, compound

HRID 2202740Notes

Reaction equation

HRID 2202740 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:49])[C:7]=1[CH:8]([O:41][Si](CC)(CC)CC)[CH2:9][N:10]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[C:11]([C:13]1[CH:14]=[N:15][N:16]([C@H:22]2[CH2:27][CH2:26][C@H:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]2)[C:17]=1[C:18]([F:21])([F:20])[F:19])=[O:12].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:49][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[CH:8]([OH:41])[CH2:9][N:10]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[C:11]([C:13]1[CH:14]=[N:15][N:16]([C@H:22]2[CH2:23][CH2:24][C@H:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:26][CH2:27]2)[C:17]=1[C:18]([F:21])([F:20])[F:19])=[O:12]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178472404HCID 178472404, compound

Product 1

HCID 178472403HCID 178472403, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of compound 1-1 (15 g, 20.2 mmol) in THF (20 mL) was added TBAF (1.0 M in THF, 40.4 mL, 40.4 mmol) dropwise at 0° C., and the mixture was allowed to warm up from 0° C. to room temperature while stirred for 2 h. The reaction mixture was quenched with saturated aqueous NH4Cl (100 mL) and extracted with EtOAc (2×150 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent: 70% EtOAc/hexane) to provide compound 1-2 (9.9 g, 84% over two steps) as a yellow-brown gum. 1H NMR (CDCl3) rotomers present δ 8.42 and 8.38 (2H, 2×s); 7.57 and 7.53 (1H, 2×s); 7.41-7.35 and 7.14-7.09 (4H, 2×m); 5.61-5.45 (1H, m); 5.10-4.50 (3H, m); 4.25-3.90 (4H, m); 3.31-3.15 (1H, m); 2.23-2.16 (6H, m); 1.65-1.51 (2H, m); 1.28-1.23 (3H, m); LCMS: 631 (M+H)+.

Workup

  1. temperatureto warm up from 0° C. to room temperature
  2. customThe reaction mixture was quenched with saturated aqueous NH4Cl (100 mL)
  3. extractionextracted with EtOAc (2×150 mL)
  4. washThe combined organic layers were washed with water (100 mL), brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel, eluent: 70% EtOAc/hexane)

Sources & evidence

ORD record
ord-8aaf3bddb20f418fb947c20da8153949
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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