Tetrabutylammonium Fluoride → HCID 19904580, compound

HRID 2372512Notes

Reaction equation

HRID 2372512 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][N:8]([CH2:17]Br)[C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[F-:20].C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C>[C:1]([O:5][C:6](=[O:19])[CH2:7][N:8]([CH2:17][F:20])[C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 19904575HCID 19904575, compound

Product 1

HCID 19904580HCID 19904580, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Bromomethylbenzoyl-glycine t-butyl ester was fluorinated in 90% yield using tetrabutylammonium fluoride in acetonitrile. NMR (CHCl3) δ 7.84 (d, 2H, Ar-2,6, J=8.3Hz), 7.44 (d, 2H, Ar-3,5, J=7.9Hz), 6.66 (1H, NH), 5.44 (d, 2H, CH2F, J=47Hz), 4.15 (d, 2H, CH2 gly, J=5.0Hz), 1.51 (9H, Bu).

Sources & evidence

ORD record
ord-86b1f0893a1d4f3c9ff774b191b33de2
Source dataset
uspto-grants-1992_03
Patent number
US05098996

Reaction notes

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