Study on the Facile Preparation of S-2-(${\omega}$-aminoalkylamino) ethyl Dihydrogen Phosphorothioates

티오인산이수소 S-2-(${\omega}$-아미노알킬아미노) 에틸들의 간편합성법 연구

  • You Sun Kim (Reactor Chemistry Laboratory, Korea Advanced Energy Research Institute) ;
  • Suc Won Kim (Reactor Chemistry Laboratory, Korea Advanced Energy Research Institute)
  • 김유선 (한국에너지연구소 원자로화학연구실) ;
  • 김석원 (한국에너지연구소 원자로화학연구실)
  • Published : 1983.12.20

Abstract

The facile route of preparing S-2-(${\omega}$-aminoalkylamino) ethyl dihydrogen phosphorothioates, potential chemical radioprotectants, have been studied. Intermediate 3-(2-phthalimidoethyl)-2-oxazolidinone was prepared by a reaction of potassium phthalimide and 3-(2-bromoethyl)-2-oxazolidinone, which was obtained through the alkaline ring closure of a mixture of carbonate and 2,2'-dibromo diethylamine prepared from diethanolamine. This was converted to N-[2-(2-bromoethylamino)ethyl] phthalimide hydrobromide by 30% HBr(gas) in acetic acid and N-(2-bromoethyl)-1,2-ethanediamine dihydrobromide was obtained by reacting the hydrobromide with a solution of HBr-HOAc. N-(2-bromoethyl)-1,3-propanediamine dihydrobromide could be prepared through the Cortese treatment of 2-(3-aminopropylamino) ethanol, which was prepared by a reaction of 1,3-diaminopropane and 2-chloroethanol. These dihydrobromides were treated by sodium thiophosphate in DMF to result S-2-(${\omega}$-aminoalkylamino) ethyl dihydrogen phosphorothioates. The characteristics of each reaction path were discussed in regards to reaction conditions and overall yields and a facile route of preparing each derivative was proposed.

Keywords

References

  1. Radiat. Res. v.54 J. M. Yuhas;J. O. Proctor;L. U. Smith
  2. J. Med. Chem. v.12 J. R. Pipper(et al.)
  3. Ref. Chem. Abstr. v.61 Asta-Wercke A. G.
  4. spring meeting, J. Korean Chem. Soc. no.spring Y. S. Kim;S. W. Kim
  5. Japan. Kokai Tokkyo Koho v.46 K. Okazaki(et al.)
  6. J. Chem. Eng. Data v.12 R. A. Hickner
  7. Private Communication on YM-08310 Yamanouchi Co.
  8. J. Amer. Chem. Soc. v.79 E. A. Steck;J. S. Burk;L. T. Fletcher
  9. annual meeting of Korean Association for Radiation Protection Y. S. Kim;S. W. Kim
  10. Fr. 1, 345, 001 Asta-Wercke A. G.
  11. Organic Synthesis v.Ⅱ F. Cortese