Dimethylformamide → Tenofovir

HRID 554463

반응식

HRID 554463 반응식
[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]

참가 물질

10

반응물 4

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

생성물 1

HCID 464205Tenofovir

시약·촉매·용매 5

HCID 111,2-Dichloroethane용매HCID 176Acetic Acid용매HCID 962Water용매HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1c01f1b6a05443549967b3ba56551380
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08049009B2

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