Tetrahydrofuran → HCID 58844833, compound

HRID 1271100Notes

Reaction equation

HRID 1271100 reaction equation
FC(F)(F)S(O)(=O)=O.C1COCC1.[O:14]=[C:15]1[N:21]2[C@H:17]([CH2:18][C:19]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][O:35][Si](CC)(CC)CC)[CH:29]=3)=[C:20]2[C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[C@H:16]1[C@H:43]([O:45][Si](CC)(CC)CC)[CH3:44].C(=O)([O-])O.[Na+]>O>[OH:45][C@@H:43]([C@H:16]1[C:15](=[O:14])[N:21]2[C@@H:17]1[CH2:18][C:19]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][OH:35])[CH:29]=1)=[C:20]2[C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[CH3:44]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 86596170HCID 86596170, compound

Product 1

HCID 58844833HCID 58844833, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Anhydrous trifluoromethanesulfonic acid was added to THF (7 ml) and water (4 ml), and the solution was adjusted to pH2.2. To the solution was added at 0° C. allyl (5R,6S)-7-oxo-6-{(1R)-1-[(triethylsilyl)oxy]ethyl}-3-(3-{[(triethylsilyl)oxy]methyl}phenyl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (520 mg). After stirring for 1 hour, thereto was added a saturated aqueous sodium hydrogencarbonate solution, and the solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to give allyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[3-(hydroxymethyl)phenyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate. This product was used in the next step without further purification.

Workup

  1. extractionthe solution 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

Sources & evidence

ORD record
ord-02b7aa9603c6427a9f574c26558e282d
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

Loading…