Tetrabutylammonium Fluoride → HCID 178521309, compound

HRID 2202743Notes

Reaction equation

HRID 2202743 reaction equation
[Si]([O:8][NH:9][C:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([N:18]2[C:22]([C:23]([F:26])([F:25])[F:24])=[C:21]([C:27]([N:29]([CH2:39][C:40]([C:42]3[C:47]([Cl:48])=[CH:46][N:45]=[CH:44][C:43]=3[Cl:49])=[O:41])[CH2:30][C:31]3[CH:36]=[C:35]([F:37])[CH:34]=[C:33]([F:38])[CH:32]=3)=[O:28])[CH:20]=[N:19]2)[CH2:14][CH2:13]1)=[O:11])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:49][C:43]1[CH:44]=[N:45][CH:46]=[C:47]([Cl:48])[C:42]=1[C:40](=[O:41])[CH2:39][N:29]([CH2:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[C:33]([F:38])[CH:32]=1)[C:27]([C:21]1[CH:20]=[N:19][N:18]([C@H:15]2[CH2:14][CH2:13][C@H:12]([C:10](=[O:11])[NH:9][OH:8])[CH2:17][CH2:16]2)[C:22]=1[C:23]([F:26])([F:24])[F:25])=[O:28]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178455400HCID 178455400, compound

Product 1

HCID 178521309HCID 178521309, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of compound 5-5 (100 mg, 0.13 mmol) in THF (8 mL) was added TBAF (1 M in THF, 0.20 mL, 0.20 mmol) dropwise and the mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with MeOH (2 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine (2×10 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 7% MeOH/DCM as eluent) to provide the compound of example 5 (19 mg, 22%) as a white solid. 1H NMR (CDCl3) rotamers present δ 8.54 and 8.48 (2H, 2×s); 7.64 and 7.60 (1H, 2×s); 6.84-6.68 (3H, m); 4.82-4.25 (5H, m); 2.23-2.04 (7H, m); 1.83-1.73 (2H, m); LCMS (APCI): 634 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with MeOH (2 mL)
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic layers were washed with brine (2×10 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel, 7% MeOH/DCM as eluent)

Sources & evidence

ORD record
ord-9a3e3bb0af66402ba0dcd11c79139d92
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

Loading…