Home A New Method for the Preparation of Ifosfamide and Cyclophosphamide
Article
Licensed
Unlicensed Requires Authentication

A New Method for the Preparation of Ifosfamide and Cyclophosphamide

  • I Neda , R Sonnenburg , R Schmutzler , U Niemeyer , B Kutscher , J Engel and A Kleemann
Published/Copyright: June 2, 2014
Become an author with De Gruyter Brill
Author Information Explore this Subject
Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 52 Issue 8

The reaction of 2-chloro-3-(2-chloroethyl)-tetrahydro-2H-1,3,2-oxazaphosphorin-2-oxide 1 and 2-chloro-tetrahydro-2H-1,3,2-oxazaphosphorin-2-oxide 2 with 2-(trimethylsilyloxy)ethylamine 3 and bis-[2-(trimethylsiloxy)ethyl]amine 4, respectively, yielded the trimethylsilylated compounds 5 and 6, analogous to ifosfamide and cyclophosphamide. The reaction of 5 and 6 with 2-chloro-1,3,5-trimethyl-1,3,5-triaza-2-phosphorin-4,6-dione 7 led to the diphosphorus compounds 8 and 9 which could be transformed to ifosfamide 11 and cyclophosphamide 12 by treatment with sulfuryl chloride. This synthesis shows that the alkylating agents 2- chloroethylammonium chloride and bis-(2-chloroethyl)ammonium chloride can be avoided and the chlorine atom can be introduced in the final reaction step of the synthesis of 11 and 12.

Keywords: Ifosfamide; Cyclophosphamide; Oxazaphosphorines; 2-(Trimethylsiloxy)ethylamines
Received: 1997-4-24
Published Online: 2014-6-2
Published in Print: 1997-8-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Chlormethylchlorphosphane mit sperrigen Substituenten -Synthese und reduktive Enthalogenierung mit Fe2(CO)9 / Bulky Chloromethylchlorophosphines -Syntheses and Reductive Dehalogenation with Fe2 (CO)9
  2. Ein neues Verfahren zur numerischen Berechnung des Madelung-Anteils der Gitterenergie ionischer Kristalle / A New Method for the Numerical Calculation of the Madelung Contribution of the Lattice Energy in Ionic Crystals
  3. Synthesis and Crystal Structure of a Caesium Hydrogen Benzoylcyanoximate Complex with 18-Crown-6: Cs(18-Crown-6){H(L)2}
  4. Darstellung und Kristallstruktur von P4O8 / Preparation and Crystal Structure of P4O8
  5. Die Fulven-Route zum Pentaisopropylcyclopentadienid / The Fulvene Route to Pentaisopropylcyclopentadienide
  6. Synthese, Struktur-und EPR-Untersuchungen an 57Fe-markiertem Tetra-n-butylammonium-bis(1,1-dicyanoethen-2,2-dithiolato)nitrosyleisen(I), (n-Bu4N)2 [57Fe(NO)(i-mnt)2] / Synthesis, Structural, and EPR Investigations on 57Fe Enriched Tetra-n-butylammonium- bis(1,1-dicyanoethene-2,2-dithiolato)nitrosyliron(I), (n-Bu4N)2[57Fe(NO)(i-mnt)2]
  7. Hydrogenation of Toluene over La0.8Sr0.2Fe1-xCoxO3-z Perovskite Catalysts
  8. Darstellung, 11B-,13C-,1H-NMR- und Schwingungsspektren von Phenylundecahydro-closo-dodecaborat(2-) sowie Kristallstruktur von [As(C6H5)4]2[(C6H5)B12H11] / Preparation, 11B-, 13C-, 1H-NMR- and Vibrational Spectra of Phenylundecahydro-closo-dodecaborate(2-) and Crystal Structure of [As(C6H5)4]2[(C6H5)B12H11]
  9. Darstellung, 11B-, 1H-NMR und Schwingungsspektren von 4-Aminopyridylundecahydro-closo-dodecaborat(1-) sowie Kristallstruktur von (Ph4As)[(4-(NH)-C5H4N)B12H11]·2CH3CN / Synthesis, 11B , 1H NMR and Vibrational Spectra of 4-Aminopyridylundecahydro-closo- dodecaborate(1-) and Crystal Structure of (Ph4As)[(4-(NH)-C5H4N)B12H11]·2CH3CN
  10. A New Method for the Preparation of Ifosfamide and Cyclophosphamide
  11. N-Boryl-Substituted Bis(amino)stannylenes and -plumbylenes
  12. CuX (X = Br, I) Oligomers and Polymerie Chains in Tetramethylcyclotetra- arsoxane-Bridged Networks [CunXn{cyclo-(CH3AsO)4}2] (n = 4, 6, 8)
  13. Über die Bildung von N,N-Bistrifluormethylhydroxylammoniumsalzen (CF3)2N(X)OX+MF6- (X = H, D; M = As, Sb) / On the Formation of N,N-Bistrifluoromethylhydroxylammonium Salts (CF3)2N(X)OX+MF6- (X = H, D; M = As, Sb)
  14. Kristallstrukturen, Schwingungsspektren und Normalkoordinaten- analysen von cis- und trans-[OsX2(acac)2], X = Cl, Br, I / Crystal Structures, Vibrational Spectra and Normal Coordinate Analyses of cis- and trans-[OsX2(acac)2], X = Cl, Br, I
  15. Darstellung und Kristallstruktur von [P(C6H5)4]2[2-SnCl2(C6H5)B10H9] / Synthesis and Crystal Structure of [P(C6H5)4]2 [2-SnCl2(C6H5)B10H9]
  16. Synthesis and Crystal Structure of Tetraphenylarsonium Pentachlorocarbonylosmate(IV), (Ph4As)[OsCl5(CO)]
  17. Kurze O-O-Abstände einer gemeinsamen Polyederkante bei Verknüpfung von PO4-Tetraedern mit VO6-Oktaedern im Vanadyl-Orthophosphat CaNi(VO)(PO4)2 / Short O-O Distances in Edge Sharing PO4 Tetrahedra and VO6 Octahedra of the Vanadyl- Orthophosphate CaNi(VO)(PO4)2
  18. SrZn(VO)(PO4)2 und BaCd(VO)(PO4)2: Zum BaZn(VO)(PO4)2-Typ verwandte, jedoch nicht isotype Vanadylphosphate / SrZn(VO)(PO4)2 and BaCd(VO)(PO4)2: Vanadylphosphates Related but not Isotypic to the BaZn(VO)(PO4 )2 Type
  19. Über ein cadmiumreiches Orthovanadat Ba2,5Cd11(VO4)9 mit Cadmium in oktaedrischer und tetragonal pyramidaler Koordination / On a Cadmium Rich Orthovanadate Ba2,5Cd11(VO4)9 Showing Cadmium in Octahedral and Square Pyramidal Coordination
  20. Transition Metal Complexes of Diazenes, XL [1] Iron Carbonyl Assisted Formation of Bicyclic 1,2-Dihydropyrazol-3-ones from Pyrazolines and Alkynes
  21. Polysulfonylamine, XC [1] Carbonsäure-Dimere, Wasser-Dimere und 18-Krone-6-Moleküle als Baugruppen eines supramolekularen Kettenpolymers: Darstellung und Struktur von (CH2CH2O)6 • 4H2O • 2HN(SO2C6H4-4-COOH)2 / Polysulfonylamines, XC [1] Carboxylic Acid Dimers, Water Dimers and 18-Crown-6 Molecules as Building Blocks in a Supramolecular Chain Polymer: Synthesis and Structure of (CH2CH2O)6 · 4H2O · 2HN(SO2C6H4-4-COOH)2
  22. Synthese und Eigenschaften von trans-Bisnitro-phthalocyaninato(2-)iridat(III) und Pyridin-nitro-phthalocyaninato(2-)iridium(III); Kristallstruktur von linear- Bis(triphenylphosphin)iminium-trans-Bisnitro-phthalocyaninato(2-)iridat(III) / Synthesis and Properties of trans-Bisnitro-phthalocyaninato(2-)iridate(III) and Pyridine-nitro-phthalocyaninato(2-)iridium(III); Crystal Structure of linear- Bis(triphenylphosphine)iminium trans-Bisnitro-phthalocyaninato(2-)iridate(III)
  23. Mehrkernige CpZr(IV)-und CpHf(IV)-Komplexe mit Oximatobrücken / Polynuclear CpZr(IV) and CpHf(IV) Complexes with Oximato Bridges
  24. Notizen: Determination of Signs of Coupling Constants for (Ethene)bis- (triphenylphosphane)platinum(0)
https://doi.org/10.1515/znb-1997-0810
Keywords for this article
Ifosfamide; Cyclophosphamide; Oxazaphosphorines; 2-(Trimethylsiloxy)ethylamines

Articles in the same Issue

  1. Chlormethylchlorphosphane mit sperrigen Substituenten -Synthese und reduktive Enthalogenierung mit Fe2(CO)9 / Bulky Chloromethylchlorophosphines -Syntheses and Reductive Dehalogenation with Fe2 (CO)9
  2. Ein neues Verfahren zur numerischen Berechnung des Madelung-Anteils der Gitterenergie ionischer Kristalle / A New Method for the Numerical Calculation of the Madelung Contribution of the Lattice Energy in Ionic Crystals
  3. Synthesis and Crystal Structure of a Caesium Hydrogen Benzoylcyanoximate Complex with 18-Crown-6: Cs(18-Crown-6){H(L)2}
  4. Darstellung und Kristallstruktur von P4O8 / Preparation and Crystal Structure of P4O8
  5. Die Fulven-Route zum Pentaisopropylcyclopentadienid / The Fulvene Route to Pentaisopropylcyclopentadienide
  6. Synthese, Struktur-und EPR-Untersuchungen an 57Fe-markiertem Tetra-n-butylammonium-bis(1,1-dicyanoethen-2,2-dithiolato)nitrosyleisen(I), (n-Bu4N)2 [57Fe(NO)(i-mnt)2] / Synthesis, Structural, and EPR Investigations on 57Fe Enriched Tetra-n-butylammonium- bis(1,1-dicyanoethene-2,2-dithiolato)nitrosyliron(I), (n-Bu4N)2[57Fe(NO)(i-mnt)2]
  7. Hydrogenation of Toluene over La0.8Sr0.2Fe1-xCoxO3-z Perovskite Catalysts
  8. Darstellung, 11B-,13C-,1H-NMR- und Schwingungsspektren von Phenylundecahydro-closo-dodecaborat(2-) sowie Kristallstruktur von [As(C6H5)4]2[(C6H5)B12H11] / Preparation, 11B-, 13C-, 1H-NMR- and Vibrational Spectra of Phenylundecahydro-closo-dodecaborate(2-) and Crystal Structure of [As(C6H5)4]2[(C6H5)B12H11]
  9. Darstellung, 11B-, 1H-NMR und Schwingungsspektren von 4-Aminopyridylundecahydro-closo-dodecaborat(1-) sowie Kristallstruktur von (Ph4As)[(4-(NH)-C5H4N)B12H11]·2CH3CN / Synthesis, 11B , 1H NMR and Vibrational Spectra of 4-Aminopyridylundecahydro-closo- dodecaborate(1-) and Crystal Structure of (Ph4As)[(4-(NH)-C5H4N)B12H11]·2CH3CN
  10. A New Method for the Preparation of Ifosfamide and Cyclophosphamide
  11. N-Boryl-Substituted Bis(amino)stannylenes and -plumbylenes
  12. CuX (X = Br, I) Oligomers and Polymerie Chains in Tetramethylcyclotetra- arsoxane-Bridged Networks [CunXn{cyclo-(CH3AsO)4}2] (n = 4, 6, 8)
  13. Über die Bildung von N,N-Bistrifluormethylhydroxylammoniumsalzen (CF3)2N(X)OX+MF6- (X = H, D; M = As, Sb) / On the Formation of N,N-Bistrifluoromethylhydroxylammonium Salts (CF3)2N(X)OX+MF6- (X = H, D; M = As, Sb)
  14. Kristallstrukturen, Schwingungsspektren und Normalkoordinaten- analysen von cis- und trans-[OsX2(acac)2], X = Cl, Br, I / Crystal Structures, Vibrational Spectra and Normal Coordinate Analyses of cis- and trans-[OsX2(acac)2], X = Cl, Br, I
  15. Darstellung und Kristallstruktur von [P(C6H5)4]2[2-SnCl2(C6H5)B10H9] / Synthesis and Crystal Structure of [P(C6H5)4]2 [2-SnCl2(C6H5)B10H9]
  16. Synthesis and Crystal Structure of Tetraphenylarsonium Pentachlorocarbonylosmate(IV), (Ph4As)[OsCl5(CO)]
  17. Kurze O-O-Abstände einer gemeinsamen Polyederkante bei Verknüpfung von PO4-Tetraedern mit VO6-Oktaedern im Vanadyl-Orthophosphat CaNi(VO)(PO4)2 / Short O-O Distances in Edge Sharing PO4 Tetrahedra and VO6 Octahedra of the Vanadyl- Orthophosphate CaNi(VO)(PO4)2
  18. SrZn(VO)(PO4)2 und BaCd(VO)(PO4)2: Zum BaZn(VO)(PO4)2-Typ verwandte, jedoch nicht isotype Vanadylphosphate / SrZn(VO)(PO4)2 and BaCd(VO)(PO4)2: Vanadylphosphates Related but not Isotypic to the BaZn(VO)(PO4 )2 Type
  19. Über ein cadmiumreiches Orthovanadat Ba2,5Cd11(VO4)9 mit Cadmium in oktaedrischer und tetragonal pyramidaler Koordination / On a Cadmium Rich Orthovanadate Ba2,5Cd11(VO4)9 Showing Cadmium in Octahedral and Square Pyramidal Coordination
  20. Transition Metal Complexes of Diazenes, XL [1] Iron Carbonyl Assisted Formation of Bicyclic 1,2-Dihydropyrazol-3-ones from Pyrazolines and Alkynes
  21. Polysulfonylamine, XC [1] Carbonsäure-Dimere, Wasser-Dimere und 18-Krone-6-Moleküle als Baugruppen eines supramolekularen Kettenpolymers: Darstellung und Struktur von (CH2CH2O)6 • 4H2O • 2HN(SO2C6H4-4-COOH)2 / Polysulfonylamines, XC [1] Carboxylic Acid Dimers, Water Dimers and 18-Crown-6 Molecules as Building Blocks in a Supramolecular Chain Polymer: Synthesis and Structure of (CH2CH2O)6 · 4H2O · 2HN(SO2C6H4-4-COOH)2
  22. Synthese und Eigenschaften von trans-Bisnitro-phthalocyaninato(2-)iridat(III) und Pyridin-nitro-phthalocyaninato(2-)iridium(III); Kristallstruktur von linear- Bis(triphenylphosphin)iminium-trans-Bisnitro-phthalocyaninato(2-)iridat(III) / Synthesis and Properties of trans-Bisnitro-phthalocyaninato(2-)iridate(III) and Pyridine-nitro-phthalocyaninato(2-)iridium(III); Crystal Structure of linear- Bis(triphenylphosphine)iminium trans-Bisnitro-phthalocyaninato(2-)iridate(III)
  23. Mehrkernige CpZr(IV)-und CpHf(IV)-Komplexe mit Oximatobrücken / Polynuclear CpZr(IV) and CpHf(IV) Complexes with Oximato Bridges
  24. Notizen: Determination of Signs of Coupling Constants for (Ethene)bis- (triphenylphosphane)platinum(0)
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 25.7.2025 from https://www.degruyterbrill.com/document/doi/10.1515/znb-1997-0810/html
Scroll to top button