Tetrabutylammonium Fluoride → HCID 57081651, compound

HRID 279051Notes

Reaction equation

HRID 279051 reaction equation
C[Si](C)(C)CCOC[N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]2=[O:30])=[CH:16][CH:15]=1)=[O:13].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]2=[O:30])=[CH:16][CH:15]=1)=[O:13]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57075463HCID 57075463, compound

Product 1

HCID 57081651HCID 57081651, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-([(5S)-N-(4-[1-(2-trimethylsilylethoxymethyl)pyrrol-2-ylcarbonyl]phenyl)-2-oxooxazolidin-5-yl]methyl)acetamide (0.79 g, 1.72 mM) in dry THF (15 ml) was stirred under nitrogen and treated dropwise with a solution of tetrabutylammonium fluoride in THF (1 M, 8.6 mM). The solution was stirred for 2.5 hours and then heated at reflux for 4 hours. The solution was evaporated and the residue partitioned between EtOAc and water. The organic layer was washed with water, dried (Mg SO4) and evaporated. The residue was purified by column chromatography, eluting with a gradient increasing in polarity from 2% to 10% MeOH/dichloromethane to give the title product as a solid (0.16 g). Mp 202-205° C., MS: 328 (MH+). NMR: 1.97 (3H, s); 3.42 (nH+H2O); 3.58 (2H, t); 3.94 (1H, m); 4.32 (1H, t); 4.89 (1H, m); 6.40 (1H, m); 6.93 (1H, m); 7.32 (1H, m); 7.82 (2H, d); 8.01 (2H, d); 8.37 (1H, t); 12.10 (1H, s).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. customThe solution was evaporated
  4. customthe residue partitioned between EtOAc and water
  5. washThe organic layer was washed with water
  6. dry with materialdried (Mg SO4)
  7. customevaporated
  8. customThe residue was purified by column chromatography
  9. washeluting with a gradient
  10. temperatureincreasing in polarity from 2% to 10% MeOH/dichloromethane

Sources & evidence

ORD record
ord-0f8740f4c0264883b82f2ac936af229e
Source dataset
uspto-grants-2002_03
Patent number
US06362191B1

Reaction notes

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