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Dimethylformamide → Tenofovir

HRID 554463
ノート
印刷プレビュー

反応式

HRID 554463 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

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

生成物 1

HCID 464205Tenofovir

試薬・触媒・溶媒 5

HCID 111,2-Dichloroethane
溶媒
HCID 176Acetic Acid溶媒
HCID 962Water溶媒
HCID 6212Chloroform溶媒
HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1c01f1b6a05443549967b3ba56551380
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08049009B2

反応ノート

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