Oxygen → Carboprost tromethamine

A solution of 15-methyl-PGF2α (185 mg.) in 2.5 ml. of an anhydrous, oxygen-free xylene containing 2,2'-dipyridyl disulfide (165 mg.) and triphenylphosphine (196 mg.) is stirred under nitrogen for 2.5 hr. at 25° C. The mixture is diluted with 150 ml. of xylene and heated at reflux for 3 hr. TLC (80 percent EtOAc/hexane) shows essentially a single, less polar product. The xylene is removed by evaporation at reduce pressure to afford a residue which is diluted with ice/water/sodium bicarbonte and ethyl acetate and extracted thoroughly with ethyl acetate. The ethyl acetate extract is washed with brine, dried over anhydrous sodium sulfate and concentrated to afford a residue of (15S)-15-methyl PGF2α, 1,9-lactone. The residue is purified by chromatography on 50 g of neutral silca packed with 10 percent acetone/methylene chloride and eluted (5 ml. fractions) with 200 ml. of 10 percent acetone/methylene chloride, 1500 ml. of 20 percent acetone/methylene chloride and 1000 ml. of 35 percent acetone/methylene chloride.

1. customat 25° C
2. additionThe mixture is diluted with 150 ml
3. temperatureat reflux for 3 hr
4. customThe xylene is removed by evaporation
5. customto afford a residue which
6. extractionextracted thoroughly with ethyl acetate
7. extractionThe ethyl acetate extract
8. washis washed with brine
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated

ORD-Eintrag

ord-effc111d35bf49fbb0448f6e364072e1

Quelldatensatz

uspto-grants-1977_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04049678