Phosphate → HCID 13388608, compound

Temperature

3 °C

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 concentarted 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.

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

ORD record

ord-4c21c94ddda6477cae60aafe75eb1535

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07018997B2