Pyridine → HCID 13591262, compound

Temperature

0 °C

0.4 ml (5 mmols--2.5 equivalents) of pyridine and then, all at once, 0.83 g (4 mmols--2 equivalents) of phosphorus pentachloride were added to a solution, cooled to -20° C., of 749 mg (2 mmols) of tert.-butyl (6R, 7R)-7-benzoylamino-3-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate in 3.7 ml of anhydrous methylene chloride. The mixture was stirred at 0° C. for 10 minutes and at +15° C. for 1 hour and cooled to -60° C., 12.2 ml of precooled anhydrous methanol were added rapidly and the mixture was subsequently stirred at room temperature for 30 minutes. It was then cooled to -15° C., 1.6 ml of distilled diethylamine was added and stirring was continued for 10 minutes at about -10° C. and the mixture was poured into ice-cold saturated NaHCO 3 solution, for working up. The mixture was extracted several times with methylene chloride and the extract was washed with water and dried over MgSO4. The solvent was evaporated off in vacuo and the residue was chromatographed on 60 g of silica gel (ethyl acetate:acetone 85:15). 158 mg (29%) of the title compound were obtained as a light rigid foam, RF : 0.33 (ethyl acetate:acetone 85:15).

1. temperaturecooled to -60° C.
2. stirringthe mixture was subsequently stirred at room temperature for 30 minutes
3. temperatureIt was then cooled to -15° C.
4. stirringstirring
5. waitwas continued for 10 minutes at about -10° C.
6. extractionThe mixture was extracted several times with methylene chloride
7. washthe extract was washed with water
8. dry with materialdried over MgSO4
9. customThe solvent was evaporated off in vacuo
10. customthe residue was chromatographed on 60 g of silica gel (ethyl acetate:acetone 85:15)

ORD record

ord-34debccff4884cab92bb9344baf27ee0

Source dataset

uspto-grants-1986_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04616084