Carbon Disulfide → HCID 13730272, Verbindung

Temperatur

-20 °C

5.3 g of 2-acetylthio-1,3-bis(p-nitrobenzyloxycarbonylamino)propane in a mixture of 161 ml of methanol and 40 ml of tetrahydrofuran were cooled to -20° C. To the solution were added 9.95 ml of a methanolic solution of sodium methoxide containing 1 mM of sodium methoxide per 1 ml of methanol. The mixture was stirred at -10° to -15° C. for 30 minutes, after which it was mixed with 0.961 ml of carbon disulphide and stirred at -20° C. for 15 minutes. Then 20 ml of a methanolic solution containing 3.59 g of 4-acetoxy-3-[1-(R)-t-butyldimethylsilyloxyethyl)-2-azetidinone was added to the above mixture and stirred at -20° C. for 1 hour. The mixture was cooled to -50° C. and then poured into a mixture of 20 ml of acetic acid and 200 ml of water. The mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulphate. The solvent was distilled off and the residue was subjected to medium pressure column chromatography througn silica gel, eluted with 3:1-2:1 by volume mixtures of benzene and ethyl acetate, to give 6.1 g of the desired compound.

1. stirringstirred at -20° C. for 15 minutes
2. additionwas added to the above mixture
3. stirringstirred at -20° C. for 1 hour
4. temperatureThe mixture was cooled to -50° C.
5. extractionThe mixture was extracted with ethyl acetate
6. washThe extract was washed with a saturated aqueous solution of sodium chloride
7. dry with materialdried over anhydrous sodium sulphate
8. distillationThe solvent was distilled off
9. washeluted with 3:1-2:1 by volume mixtures of benzene and ethyl acetate

ORD-Eintrag

ord-fd153148a334471a80be5c976744feec

Quelldatensatz

uspto-grants-1986_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04613595