Tetrabutylammonium Fluoride → HCID 90414185, compound

HRID 1522018Notes

Reaction equation

HRID 1522018 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]1[CH:21]=[CH:22][C:23]([O:60][CH3:61])=[C:24]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]3[NH:32][C:33]([C:35]4[CH2:40][C@@H:39]([CH2:41][O:42][Si](C(C)C)(C(C)C)C(C)C)[N:38]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:37][CH:36]=4)=[CH:34][C:27]=23)[CH:25]=1>O1CCCC1>[F:19][C:20]1[CH:21]=[CH:22][C:23]([O:60][CH3:61])=[C:24]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]3[NH:32][C:33]([C:35]4[CH2:40][C@@H:39]([CH2:41][OH:42])[N:38]([C:53]([O:55][C:56]([CH3:57])([CH3:58])[CH3:59])=[O:54])[CH2:37][CH:36]=4)=[CH:34][C:27]=23)[CH:25]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90411895HCID 90411895, compound

Product 1

HCID 90414185HCID 90414185, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1M tetrabutylammonium fluoride in tetrahydrofuran (3.1 mL, 3.10 mmol) was added to a solution of Example 260E (627 mg, 1.028 mmol) in tetrahydrofuran (5 mL) and the mixture was stirred at room temperature for 1 hour and concentrated. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 0-7% methanol-dichloromethane to give the title compound. MS (ESI+) m/z 454.1 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography on silica gel
  3. washeluting with a gradient of 0-7% methanol-dichloromethane

Sources & evidence

ORD record
ord-503c737b65a546fa883b0526adcdaded
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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