Tetrabutylammonium Fluoride → HCID 6474953, compound

HRID 480674Notes

Reaction equation

HRID 480674 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 10650455HCID 10650455, compound

Product 1

HCID 6474953HCID 6474953, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 25 (278 mg, 0.499 mmol) in CH3CN (15 mL) was treated with tetra-n-butylammoniumfluorid (I M solution in THF) (0.6 mL, 0.6 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 27 (151 mg, 95 as a white solid: mp 176-177° C.; [α]D+6.5 (c 0.47, MeOH); UV (MeOH) λmax 249.5 (ε 15600), 291.0 nm 11700) (pH 7), 248.5 (ε 16300), 291.5 nm (ε 11800) (pH 2), 253.5 (ε 16500), 284.5 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-3bbf38928e144d1396fdf2a9f33a0ab7
Source dataset
uspto-grants-2003_11
Patent number
US06653318B1

Reaction notes

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