Triethylamine → HCID 53920907, compound

1.33 ml of triethylamine and 0.36 ml of diethyl cyanophosphonate were added, whilst ice-cooling and stirring, to a suspension of 322 mg of (4R,5R)-5-methyl-2-oxothiazolidine-4-carboxylic acid and 406 mg of N-(2-nitrooxyethyl)amine nitrate in 40 ml of dry tetrahydrofuran, and the resulting mixture was stirred at room temperature for 1 hour and 25 minutes. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was mixed with ethyl acetate. The resulting mixture was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residual yellow oil thus obtained was purified by column chromatography through silica gel, using a 20:1 by volume mixture of methylene chloride and methanol as the eluent, to give 324 mg of the title compound as a pale yellow oil.

1. temperaturecooling
2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
3. additionthe residue was mixed with ethyl acetate
4. washThe resulting mixture was washed with a saturated aqueous solution of sodium chloride
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was removed by distillation under reduced pressure
7. customthe residual yellow oil thus obtained
8. customwas purified by column chromatography through silica gel
9. additionby volume mixture of methylene chloride and methanol as the eluent

ORD record

ord-72ae95657010473f8f738265a881399e

Source dataset

uspto-grants-1994_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05298516