Tetrabutylammonium Fluoride → HCID 86708067, compound

HRID 1524364Notes

Reaction equation

HRID 1524364 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([N:39]([S:45]([C:48]1[CH:53]=[CH:52][C:51]([CH2:54][O:55][Si](C(C)(C)C)(C)C)=[CH:50][CH:49]=1)(=[O:47])=[O:46])[CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:11][CH2:12][C:13]([F:38])([F:37])[CH2:14][NH:15][C:16](=[O:36])[C@H:17]([CH:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH:18][C:19]([O:21][CH3:22])=[O:20])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:38][C:13]([F:37])([CH2:12][CH2:11][C@H:10]([N:39]([S:45]([C:48]1[CH:49]=[CH:50][C:51]([CH2:54][OH:55])=[CH:52][CH:53]=1)(=[O:47])=[O:46])[CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:9][OH:8])[CH2:14][NH:15][C:16](=[O:36])[C@H:17]([CH:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[NH:18][C:19]([O:21][CH3:22])=[O:20]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86708066HCID 86708066, compound

Product 1

HCID 86708067HCID 86708067, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of the material from Step 11 (51 mg, 0.056 mmol) in THF (1 mL) at 0° C. was added 1.0 M TBAF (111 μL, 0.11 mmol) in THF. The reaction mixture was stirred at room temperature overnight, concentrated to dryness in vacuo, and the residue was purified by flash chromatography on silica gel using EtOAc-hexanes to afford 30 mg of the title compound. 1H NMR (DMSO-d6): δ 8.37 (b, 1H), 7.76 (d, J=7.92 Hz, 2H), 7.49 (d, J=7.92 Hz, 2H), 7.46 (d, J=9.20 Hz, 1H), 7.37-7.30 (m, 4H), 7.30-7.18 (m, 4H), 7.17-7.09 (m, 2H), 5.41 (t, J=5.68 Hz, 1H), 5.10-5.00 (m, 1H), 4.74 (b, 1H), 4.59 (d, J=5.61 Hz, 2H), 4.27 (d, J=11.54 Hz, 1H), 3.63-3.51 (m, 1H), 3.42 (s, 3H), 3.39-3.15 (m, 2H), 3.27-3.20 (m, 2H), 3.12-2.90 (m, 2H), 1.65-1.06 (m, 10H), 0.84 (t, J=7.24 Hz, 3H).

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-c28f2643811e41f3b12547925af30d60
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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