Dimethylformamide → Tenofovir

HRID 554463

Reaktionsgleichung

Reaktionsgleichung von HRID 554463
[OH:1][C@H:2]([CH3:14])[CH2:3][N:4]1[CH:12]=[N:11][C:10]2[C:5]1=[N:6][CH:7]=[N:8][C:9]=2[NH2:13].CC[O:17][P:18]([O:32]CC)([CH2:20]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:19].CC(C)([O-])C.[Mg+2].CC(C)([O-])C.CN(C)C=O>O.C(Cl)CCl.C(Cl)(Cl)Cl.C(Cl)Cl.C(O)(=O)C>[P:18]([CH2:20][O:1][C@H:2]([CH3:14])[CH2:3][N:4]1[CH:12]=[N:11][C:10]2[C:5]1=[N:6][CH:7]=[N:8][C:9]=2[NH2:13])([OH:32])([OH:19])=[O:17]

Komponenten

10

Edukt 4

HCID 6228DimethylformamideHCID 4452119-(2-Hydroxypropyl)adenine, (R)-HCID 4193599Diethyl P-[[[(4-methylphenyl)sulfonyl]oxy]methyl]phosphonateHCID 12040442Magnesium 2-methylpropan-2-olate

Produkt 1

HCID 464205Tenofovir

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Accordingly (R)-9-[2-(hydroxyl)propyl]adenine is condensed with Diethyl p-toluene sulfonyloxy methylphosphonate in presence of Magnesium tert-butoxide in a polar solvent preferably dimethylformamide at a temperature of 70° C. to 80° C. After the reaction completion the reaction mass is neutralized by adding an acid preferably acetic acid and the solvent is distilled off completely. The obtained crude is dissolved in a chlorinated hydrocarbon selected from Methylenedichloride, chloroform, and Ethylene dichloride and water is added. The reaction mixture is filtered to remove the salts and Methylenedichloride layer is separated. Methylenedichloride is distilled off completely to get (R)-9-[2-(phosphonomethoxy)propyl]adenine.

Aufarbeitung

  1. distillationthe solvent is distilled off completely
  2. customThe obtained crude
  3. additionis added
  4. filtrationThe reaction mixture is filtered
  5. customto remove the salts and Methylenedichloride layer
  6. customis separated
  7. distillationMethylenedichloride is distilled off completely

Quellen und Nachweise

ORD-Eintrag
ord-1c01f1b6a05443549967b3ba56551380
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08049009B2

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