Tetrabutylammonium Fluoride → HCID 25005654, compound

HRID 1175673Notes

Reaction equation

HRID 1175673 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:15][C@:14]([CH3:26])([O:16][CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])[C@@H:13]([O:27][Si](C(C)(C)C)(C)C)[C@H:12]1[O:35][Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:15][C@:14]([CH3:26])([O:16][CH2:17][P:18](=[O:25])([O:19][CH2:20][CH3:21])[O:22][CH2:23][CH3:24])[C@@H:13]([OH:27])[C@H:12]1[OH:35]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86619968HCID 86619968, compound

Product 1

HCID 25005654HCID 25005654, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of compound 31.3 (102 mg, 0.16 mmol) in THF (5 mL) was added a 1N solution of tetrabutylammonium fluoride in THF (0.15 mL, 0.5 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 31.4 (38 mg, 59% yield). 1H NMR (300 MHz, CD3OD): δ 1.28 (m, 6H), 1.52 (s, 3H), 3.62 (m, 1H), 3.80 (m, 2H), 4.02 (m, 4H), 4.11 (m, 1H), 6.15 (d, 1H, J=7.1), 8.1 (s, 1H), 8.75 (s, 1H). LRMS (ESI) MH+ C15H24N5O7P requires 418.4. Found 417.9.

Workup

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

Sources & evidence

ORD record
ord-70fb0535224b4296959f3bb2b1f9f623
Source dataset
uspto-grants-2010_11
Patent number
US07842672B2

Reaction notes

Loading…