Phosphate → HCID 13388608, compound

HRID 638873Notes

Reaction equation

HRID 638873 reaction equation
[N+](C1C=CC(C[C:9]2[S:15][CH:14]3[N:11]([C:12](=[O:34])[C:13]3(C(OC(=O)C)C3C=CC4N5C=CN=C5SC=4C=3)Br)[C:10]=2[C:35]([O-:37])=[O:36])=CC=1)([O-])=O.C(#N)C.P([O-])([O-])([O-])=O>C1COCC1.[Pd]>[O:34]=[C:12]1[N:11]2[CH:14]([S:15][CH:9]=[C:10]2[C:35]([OH:37])=[O:36])[CH2:13]1

Participants

6

Reactant 3

HCID 1061PhosphateHCID 6342AcetonitrileHCID 68704262HCID 68704262, compound

Product 1

HCID 13388608HCID 13388608, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
3 °C

Procedure

4-Nitrobenzyl-6-[(acetyloxy) (imidazo[2,1-b][1,3]benzothiazol-7-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (900 mg, 1.4 mmol) was dissolved in THF (20 mL) and acetonitrile (20 mL) and 0.5 M phosphate buffer (pH 6.5, 20 mL) and hydrogenated over Pd/C (10%) at 40 psi pressure for 6 hrs. The reaction vessel was covered with foil to exclude light. The reaction mixture was filtered, cooled to 3° C., and 0.1 N NaOH was added to adjust the pH to 8.5. The filtrate was concentrated and the aqueous layer was washed with ethyl acetate. The aqueous layer was separated. The aqueous layer was concentrated under high vacuum at 35° C. to give a yellow precipitate. The product was purified by HP21 resin reverse phase column chromatography. Initially the column was eluted with deionized water (2 L) and latter with 10% acetonitrile:water. The fractions containing the product were collected and concentrated under reduced pressure at room temperature. The yellow solid was washed with acetone, filtered and dried. Yield: 180 mg, 36%; as yellow crystals; mp 235° C.; (M+H+Na) 378.

Workup

  1. filtrationThe reaction mixture was filtered
  2. addition0.1 N NaOH was added
  3. concentrationThe filtrate was concentrated
  4. washthe aqueous layer was washed with ethyl acetate
  5. customThe aqueous layer was separated
  6. concentrationThe aqueous layer was concentrated under high vacuum at 35° C.
  7. customto give a yellow precipitate
  8. customThe product was purified by HP21 resin reverse phase column chromatography
  9. washInitially the column was eluted with deionized water (2 L) and latter with 10% acetonitrile
  10. additionThe fractions containing the product
  11. customwere collected
  12. concentrationconcentrated under reduced pressure at room temperature
  13. washThe yellow solid was washed with acetone
  14. filtrationfiltered
  15. customdried

Sources & evidence

ORD record
ord-809475625461469fbe9879e995c34944
Source dataset
uspto-grants-2010_04
Patent number
US07691842B2

Reaction notes

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