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 reduced pressure to afford a residue which is diluted with ice/water/sodium bicarbonate 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 silica 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 at reduced pressure
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 record

ord-e0b4d23c2be344eb85ff2488554c9617

Source dataset

uspto-grants-1977_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04032543