Tetrabutylammonium Fluoride → HCID 68842699, compound

HRID 1889271Notes

Reaction equation

HRID 1889271 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:20][CH2:21][CH2:22][O:23][Si](C(C)(C)C)(C)C)=[O:9])([CH3:6])[CH3:5].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][O:2][C:3](=[O:31])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:20][CH2:21][CH2:22][OH:23])=[O:9])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68841541HCID 68841541, compound

Product 1

HCID 68842699HCID 68842699, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 112 mg 2-({1-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2-methyl-propionic acid methyl ester in 1 ml abs. THF at −10° C. 0.25 ml tetra-butylammonium fluoride (1 M in THF) was added, and the reaction was stirred at 0° C. for 3 h. It was then poured onto ice-water and extracted with ethyl acetate three times. The combined organic layers were then washed with water, dried over sodium sulphate, concentrated in vacuo and crystallized from n-pentane to yield 67 mg 2-{[1-(2-hydroxy-ethoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester.

Workup

  1. customat −10° C
  2. additionIt was then poured onto ice-water
  3. extractionextracted with ethyl acetate three times
  4. washThe combined organic layers were then washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customcrystallized from n-pentane

Sources & evidence

ORD record
ord-74a2d6c6cc204328ad6482eff39217b4
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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