Tetrabutylammonium Fluoride Trihydrate → HCID 22880211, compound

HRID 1940035Notes

Reaction equation

HRID 1940035 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][C@@H:16](OS(C(F)(F)F)(=O)=O)[C@@H:15]2[C@H:12]1[C:13](=[O:37])[N:14]2[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.O.[F-:41].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:17][C@H:16]([F:41])[C@@H:15]2[C@H:12]1[C:13](=[O:37])[N:14]2[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 86751738HCID 86751738, compound

Product 1

HCID 22880211HCID 22880211, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1S,4R,5S)-6-(3,4-Dimethoxy-benzyl)-7-oxo-4-trifluoromethanesulphonyloxy-2,6-diazabicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (1.1 g, 2.02 mmol) and tetrabutylammonium fluoride trihydrate (704 mg, 2.23 mmol) were stirred together in 10 ml of tetrahydrofuran at room temperature for 10 min. Thereafter, the solvent was removed in a vacuum, the oily residue was taken up in ethyl acetate and extracted three times with water and once with saturated aqueous sodium chloride solution. The organic phase was dried over magnesium sulphate and concentrated. The residual brown oil was chromatographed over silica gel with ethyl acetate and a pale yellow oil was obtained.

Workup

  1. customThereafter, the solvent was removed in a vacuum
  2. extractionextracted three times with water
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residual brown oil was chromatographed over silica gel with ethyl acetate
  6. customa pale yellow oil was obtained

Sources & evidence

ORD record
ord-70543a5e9c364924a2357f8a0e6ea627
Source dataset
uspto-grants-1997_12
Patent number
US05698577

Reaction notes

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