Tetrabutylammonium Fluoride → HCID 10320258, compound

HRID 919016Notes

Reaction equation

HRID 919016 reaction equation
[C:1]([N:5]([C:29](=[O:38])[C:30]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[CH:31]=1)[NH:6][C:7]([C:9]1[CH:27]=[CH:26][C:12]2[O:13][CH2:14][CH:15]([CH2:17][O:18][Si](C(C)(C)C)(C)C)[O:16][C:11]=2[C:10]=1[CH3:28])=[O:8])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([N:5]([C:29](=[O:38])[C:30]1[CH:31]=[C:32]([CH3:37])[CH:33]=[C:34]([CH3:36])[CH:35]=1)[NH:6][C:7]([C:9]1[CH:27]=[CH:26][C:12]2[O:13][CH2:14][CH:15]([CH2:17][OH:18])[O:16][C:11]=2[C:10]=1[CH3:28])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10098811HCID 10098811, compound

Product 1

HCID 10320258HCID 10320258, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a round bottom flask equipped with magnetic stirring was added 3,5-dimethylbenzoic acid N-tert-butyl-N′-[3-(tert-butyldimethylsilyloxymethyl)-5-methyl-2,3-dihydrobenzo[1,4]dioxine-6-carbonyl]-hydrazide (0.26 g, 0.48 mmol), THF (5.0 mL), and 1 M solution or tetrabutylammonium fluoride (TBAF) in THF (1.39 mL, 1.39 mmol). The mixture was stirred at room temperature for three hours. The THF was evaporated and the residue was taken up in ethyl acetate. This solution was washed once with water, once with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated. The residue was triturated with hexane to give a white solid, 3,5-dimethylbenzoic acid N-tert-butyl-N′-(3-hydroxymethyl-5-methyl-2,3-dihydrobenzo[1,4]dioxine-6-carbonyl)-hydrazide, (0.205 g, 0.48 mmol) in 100% yield. 1H-NMR (300 MHz, CD3COCD3) δ (ppm): 1.59 (s, 9H), 1.89 (d, 3H), 2.25 (s, 6H), 3.79 (m, 2H), 4.04 (m, 1H), 4.18 (m, 1H), 4.33 (m, 1H), 6.33 (dd, 1H), 6.56 (dd, 1H), 7.03 (s, 1H), 7.12 (s, 2H), 9.51 (s, 1H); TLC Rf=0.03 (ether/hexane).

Workup

  1. customTo a round bottom flask equipped
  2. stirringThe mixture was stirred at room temperature for three hours
  3. customThe THF was evaporated
  4. washThis solution was washed once with water, once with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-e3eabd397ca045f2a0561815624cafa0
Source dataset
uspto-grants-2016_03
Patent number
US09272986B2

Reaction notes

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