Thiazolo[4,5-c]pyridine → (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(1-carboxycyclobutyl)oxyiminoacetyl]amino]-8-oxo-3-([1,3]thiazolo[4,5-c]pyridin-5-ium-5-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

To a solution of diphenylmethyl 7-[(Z)-2-(1-t-butoxycarbonylcyclobut-1-oxyimino)-2-(2-tritylaminothiazol-4-yl)-acetamido]-3-iodomethyl-3-cephem-4-carboxylate [VIIe'] (482 mg, 0.45 mmole) in 2 mL of DMSO was added thiazolo[4,5-c]pyridine (68 mg, 0.5 mmole) in one portion. The mixture was stirred for 45 minutes at room temperature. The reaction mixture was then diluted with ether (50 mL) and the precipitated oil was triturated in ether (4×50 mL). The precipitate was mixed with anisole (0.5 mL), trifluoroacetic acid (5 mL) and water (0.5 mL), and the mixture was stirred with ice cooling for 30 minutes and at room temperature for 1 hour, and then was concentrated under reduced pressure (<30° C.). The residue was triturated with isopropyl ether (100 mL), and the resulting precipitate was collected by filtration to afford 395 mg of crude title compound, as a yellow powder. The crude product (387 mg) was purified on an HP-20 column (100 mL). The eluate containing desired product, which was eluted with 50% methanol, was concentrated and lyophilized to give 80 mg (31%) of the title product (Ie) as a pale yellow amorphous powder. Mp >170° C. (dec.).

1. customthe precipitated oil was triturated in ether (4×50 mL)
2. additionThe precipitate was mixed with anisole (0.5 mL), trifluoroacetic acid (5 mL) and water (0.5 mL)
3. stirringthe mixture was stirred with ice cooling for 30 minutes and at room temperature for 1 hour
4. concentrationwas concentrated under reduced pressure (<30° C.)
5. customThe residue was triturated with isopropyl ether (100 mL)
6. filtrationthe resulting precipitate was collected by filtration
7. customto afford 395 mg of crude title compound
8. customThe crude product (387 mg) was purified on an HP-20 column (100 mL)
9. additionThe eluate containing desired product, which
10. washwas eluted with 50% methanol
11. concentrationwas concentrated

ORD-Eintrag

ord-ae358299d736460b9bf4830f9cced679

Quelldatensatz

uspto-grants-1985_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04500526