Tetrabutylammonium Fluoride → HCID 6474954, compound

HRID 480675Notes

Reaction equation

HRID 480675 reaction equation
[Br:1]/[CH:2]=[CH:3]/[C:4]1[C:5](=[O:35])[NH:6][C:7](=[O:34])[N:8]([C@H:10]2[O:14][C@H:13]([CH2:15][O:16][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[O:12][CH2:11]2)[CH:9]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CC#N>[Br:1]/[CH:2]=[CH:3]/[C:4]1[C:5](=[O:35])[NH:6][C:7](=[O:34])[N:8]([C@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[O:12][CH2:11]2)[CH:9]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10769154HCID 10769154, compound

Product 1

HCID 6474954HCID 6474954, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 26 (140 mg, 0.251 mmol) in CH3CN (10 mL) was treated with tetra-n-butylammoniumfluorid (I M solution in THF) (0.3 mL, 0.3 mmol) at rt for 1 h. After concentration of the mixture, the residue was purified by silica gel column chromatography (CHCl3:MeOH, 20:1) to give 28 (72 mg, 90%) as a white solid: mp 75-78° C.; [α]D−2.8 (c 0.4, MeOH); UV (MeOH) λmax 250.0 (ε 13900), 292.0 nm (ε 10600) (pH 7), 249.5 (ε 14400), 291.5 nm (ε 10800) (pH 2), 254.0 (ε 14100), 284.0 nm (sh) (pH 11).

Workup

  1. customAfter concentration of the mixture, the residue was purified by silica gel column chromatography (CHCl3:MeOH, 20:1)

Sources & evidence

ORD record
ord-3e23309b69ab4f0bbaee237273b562d4
Source dataset
uspto-grants-2003_11
Patent number
US06653318B1

Reaction notes

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