Water → HCID 23690286, compound

HRID 1241524Notes

Reaction equation

HRID 1241524 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[CH2:6][C:7]([C:25]1[CH:30]=[CH:29][C:28]([C:31]([NH:33][CH3:34])=[O:32])=[CH:27][CH:26]=1)=[C:8]2[C:12]([O:14]CC1C=CC([N+]([O-])=O)=CC=1)=[O:13])[CH3:3].O.C(=O)([O-])O.[Na+:40]>C1COCC1.[Pd]>[Na+:40].[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[CH2:6][C:7]([C:25]1[CH:26]=[CH:27][C:28]([C:31]([NH:33][CH3:34])=[O:32])=[CH:29][CH:30]=1)=[C:8]2[C:12]([O-:14])=[O:13])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 11705379HCID 11705379, compound

Product 1

HCID 23690286HCID 23690286, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-{4-[(methylamino)carbonyl]phenyl}-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (60 mg) obained in the above Step b) was dissolved in THF (6 ml) and ion-exchange water (4.7 ml), and thereto was added 0.1 N aqueous sodium hydrogen carbonate solution (1.3 ml). To the mixture was added 10% palladium on carbon (120 mg), and the mixture was subjected to hydrogenolysis for 30 minutes under atmospheric pressure at room temperature. The catalyst was removed by filtration, and washed with water, and chloroform was added to the filtrate, and extracted and separated (three times). The organic solvent in the aqueous layer was removed under reduced pressure, and the resultant was purified by polymer chromatography (CHP-20P). The fractions eluted with 0–2% aqueous THF solution were combined and lyophilized to give (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-{4-[(methylamino)carbonyl]-phenyl}-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid sodium salt (18 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with water, and chloroform
  3. additionwas added to the filtrate
  4. extractionextracted
  5. customseparated (three times)
  6. customThe organic solvent in the aqueous layer was removed under reduced pressure
  7. customthe resultant was purified by polymer chromatography (CHP-20P)
  8. washThe fractions eluted with 0–2% aqueous THF solution

Sources & evidence

ORD record
ord-4e0ec9bbb2b34d88b1d9a0fb1799ed3d
Source dataset
uspto-grants-2006_10
Patent number
US07115595B2

Reaction notes

Loading…