Tetrabutylammonium Fluoride → HCID 25006396, compound

HRID 1175670Notes

Reaction equation

HRID 1175670 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][O:10][C@:11]1([CH3:40])[C@@H:15]([O:16][Si](C(C)(C)C)(C)C)[C@@H:14]([O:24][Si](C(C)(C)C)(C)C)[C@H:13]([N:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[N:34][C:33]2=[O:39])[O:12]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:6]([O:5][P:4]([CH2:9][O:10][C@:11]1([CH3:40])[C@@H:15]([OH:16])[C@@H:14]([OH:24])[C@H:13]([N:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[N:34][C:33]2=[O:39])[O:12]1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86619967HCID 86619967, compound

Product 1

HCID 25006396HCID 25006396, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of compound 30.4 (288 mg, 0.46 mmol) in THF (20 mL) was added a 1N solution of tetrabutylammonium fluoride in THF (2.7 mL, 2.8 mmol). The mixture was stirred at r.t. for 1 h and concentrated down under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 10% MeOH in CH2Cl2 to give compound 30.5 (114 mg, 63% yield). 1H NMR (300 MHz, CD3OD): δ 1.38 (t, 6H, J=7.0), 1.40 (s, 3H), 3.86 (m, 2H), 4.02 (d, 1H, J=4.9), 4.11 (m, 4H), 4.56 (dd, 1H, J=7.0, 6.7), 5.98 (d, 1H, J=7.4), 6.11 (d, 1H, J=7.0), 7.63 (d, 1H, J=7.6). LRMS (ESI) MH+ C14H24N3O8P requires 394.4. Found 394.1.

Workup

  1. concentrationconcentrated down under reduced pressure
  2. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-6673f86ee6c7402381ac814438e244f0
Source dataset
uspto-grants-2010_11
Patent number
US07842672B2

Reaction notes

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