Tetrabutylammonium Fluoride → HCID 57907411, compound

HRID 1947714Notes

Reaction equation

HRID 1947714 reaction equation
[C:1]([O:5][C:6]([NH:8]/[N:9]=[C:10](\[C:17]#[C:18][Si](C)(C)C)/[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH:18]=[CH:17][C:10]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 87174988HCID 87174988, compound

Product 1

HCID 57907411HCID 57907411, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 77.0 g, (236 mmol) of (5Z)-5-[(tert-butoxycarbonyl)hydrazono]-7-(trimethylsilyl)hept-6-ynoic acid from step B above in 500 mL of THF was added 350 mL (350 mmol) of a 1.0 M solution of tetrabutylammonium fluoride in THF over 30 min. The resulting mixture was stirred at ambient temperature for 48 h and then evaporated to dryness in vacuo. The residue was diluted with 1 L of a 5% aqueous acetic acid solution and the aqueous phase extracted with ethyl acetate (3×350 mL). The combined organic layers were washed with water (2×100 mL), and brine (150 mL), dried over magnesium sulfate, filtered and evaporated to dryness in vacuo. The crude residue was purified by silica gel chromatography eluting with 3% acetic acid and 35% ethyl acetate in hexanes mixture to afford the title compound as yellow oil (60 g, quantitative yield). LC-MS: m/z (ES) 255 (MH)+.

Workup

  1. customevaporated to dryness in vacuo
  2. additionThe residue was diluted with 1 L of a 5% aqueous acetic acid solution
  3. extractionthe aqueous phase extracted with ethyl acetate (3×350 mL)
  4. washThe combined organic layers were washed with water (2×100 mL), and brine (150 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo
  8. customThe crude residue was purified by silica gel chromatography
  9. washeluting with 3% acetic acid and 35% ethyl acetate in hexanes mixture

Sources & evidence

ORD record
ord-acbe45e678144e7f8032cac7de782e33
Source dataset
uspto-grants-2013_03
Patent number
US08399480B2

Reaction notes

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