Tetrabutylammonium Fluoride Trihydrate → HCID 22880211, compound

HRID 726994Notes

Reaction equation

HRID 726994 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-Di methoxy-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-5c87944635b04e6b835ad7a29a4e33e1
Source dataset
uspto-grants-1998_01
Patent number
US05712268

Reaction notes

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