Tetrabutylammonium Fluoride → HCID 86708057, compound

HRID 1524354Notes

Reaction equation

HRID 1524354 reaction equation
[Si]([O:18][CH2:19][C@@H:20]([N:48]([CH2:61][CH2:62][CH:63]([CH3:65])[CH3:64])[S:49]([C:52]1[CH:57]=[CH:56][C:55]([N+:58]([O-:60])=[O:59])=[CH:54][CH:53]=1)(=[O:51])=[O:50])[CH2:21][CH2:22][CH:23]([F:47])[CH2:24][NH:25][C:26](=[O:46])[C@H:27]([CH:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH:28][C:29]([O:31][CH3:32])=[O:30])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:47][CH:23]([CH2:22][CH2:21][C@H:20]([N:48]([CH2:61][CH2:62][CH:63]([CH3:65])[CH3:64])[S:49]([C:52]1[CH:57]=[CH:56][C:55]([N+:58]([O-:60])=[O:59])=[CH:54][CH:53]=1)(=[O:51])=[O:50])[CH2:19][OH:18])[CH2:24][NH:25][C:26](=[O:46])[C@H:27]([CH:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[NH:28][C:29]([O:31][CH3:32])=[O:30]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86708056HCID 86708056, compound

Product 1

HCID 86708057HCID 86708057, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of the material from Step 13 (80 mg, 0.086 mmol) in THF (1.7 mL) was added 1.0 M TBAF (104 μL, 0.104 mmol) in THF. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, and the residue was purified by flash chromatography on silica gel using EtOAc-hexanes to afford 45 mg of the title compound. LCMS (M+1)=687.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-49ea7952b1ce4436b3a56b8b4e4e41a6
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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