Trifluoromethanesulfonic acid → HCID 58844805, compound

HRID 1271105Notes

Reaction equation

HRID 1271105 reaction equation
[CH3:1][NH:2][C:3]([O:5][CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[CH2:19][C@H:18]3[N:15]([C:16](=[O:30])[C@@H:17]3[C@H:20]([O:22][Si](CC)(CC)CC)[CH3:21])[C:14]=2[C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])[CH:10]=[CH:11][CH:12]=1)=[O:4].FC(F)(F)S(O)(=O)=O.C(=O)([O-])O.[Na+]>C1COCC1.O>[OH:22][C@@H:20]([C@H:17]1[C:16](=[O:30])[N:15]2[C@@H:18]1[CH2:19][C:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([CH2:6][O:5][C:3]([NH:2][CH3:1])=[O:4])[CH:8]=1)=[C:14]2[C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])[CH3:21]

Participants

6

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 86596172HCID 86596172, compound

Product 1

HCID 58844805HCID 58844805, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl (5R,6S)-3-[3-({[(methylamino)carbonyl]oxy}methyl)phenyl]-7-oxo-6-{(1R)-1-[(triethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (284 mg) in THF (4 ml) was added a solution of anhydrous trifluoromethanesulfonic acid (0.6 ml) in water (2 ml) at 0° C., and the solution was stirred for 25 minutes. Thereto was added a cold aqueous saturated sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol) to give allyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[3-({[(methylamino)carbonyl]oxy}methyl)phenyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (139 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-12f928a4a5654ebd81a652410e1bcb65
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

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