Phosphate → HCID 86596169, compound

HRID 1271098Notes

Reaction equation

HRID 1271098 reaction equation
[O:1]=[C:2]1[N:8]2[C@H:4]([CH2:5][C:6]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24](O[Si](C)(C)C)[CH:23]=3)=[C:7]2[C:9]([O:11]CC2C=CC([N+]([O-])=O)=CC=2)=[O:10])[C@H:3]1[C@H:33]([O:35][Si](C)(C)C)[CH3:34].C(=O)([O-])[OH:41].[Na+:44].P([O-])([O-])([O-])=O>C(#N)C.[Zn]>[OH:35][C@@H:33]([C@H:3]1[C:2](=[O:1])[N:8]2[C@@H:4]1[CH2:5][C:6]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=1[OH:41])=[C:7]2[C:9]([O-:11])=[O:10])[CH3:34].[Na+:44]

Participants

6

Reactant 3

HCID 1061PhosphateHCID 516892Sodium BicarbonateHCID 86596174HCID 86596174, compound

Product 1

HCID 86596169HCID 86596169, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 4-nitrobenzyl (5R,6S)-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-3-{3-[(trimethylsilyl)oxy]phenyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (207 mg) in acetonitrile (3 ml) was added under ice cooling 0.1N hydrochloric acid (0.3 ml), and the mixture was stirred for 15 minutes. After the solution was neutralized with a 0.1N aqueous sodium hydrogencarbonate solution (0.3 ml), further thereto 0.25M phosphate buffer (10 ml, pH6) and acetonitrile (7 ml) were added. Zinc dust (1.49 g) was added thereto and the mixture was vigorously stirred for an hour under ice cooling and for additional an hour at room temperature. The insoluble materials were removed with celite and washed with water and chloroform. Then, the filtrate and the washed solvent were combined to separate by a separating funnel. The aqueous layer was washed with chloroform, twice separated with a separating funnel and an organic solvent in the aqueous layer was removed under reduced pressure. The aqueous solution was purified by polymer chromatography (CHP-20P), and the fractions eluted with water were collected to be subjected to freeze-drying to give sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(hydroxyphenyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (14 mg).

Workup

  1. stirringthe mixture was vigorously stirred for an hour under ice cooling and for additional an hour at room temperature
  2. customThe insoluble materials were removed with celite
  3. washwashed with water and chloroform
  4. customto separate by a separating funnel
  5. washThe aqueous layer was washed with chloroform
  6. customtwice separated with a separating funnel
  7. customan organic solvent in the aqueous layer was removed under reduced pressure
  8. customThe aqueous solution was purified by polymer chromatography (CHP-20P)
  9. washthe fractions eluted with water
  10. customwere collected
  11. customto freeze-drying

Sources & evidence

ORD record
ord-8dca065170794fdaa70e18e227b71c5e
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

Loading…