Bromotrimethylsilane → Tenofovir

HRID 1890236

反応式

HRID 1890236 の反応式
C([O:3][P:4]([CH2:9][O:10][C@H:11]([CH3:23])[CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][CH:16]=[N:17][C:18]=2[NH2:22])([O:6]CC)=[O:5])C.Br[Si](C)(C)C>C(#N)C>[P:4]([CH2:9][O:10][C@H:11]([CH3:23])[CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][CH:16]=[N:17][C:18]=2[NH2:22])([OH:5])([OH:6])=[O:3]

参加物

4

反応物 2

HCID 76113BromotrimethylsilaneHCID 10947889Diethyl P-(((1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy)methyl)phosphonate

生成物 1

HCID 464205Tenofovir

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a reaction vessel was added stepwise the product (D) of step (4), acetonitrile and Bromotrimethylsilane, the mixture was refluxed while stirring until the completion of the reaction, volatile liquid was removed under vacuum, the resultant residue was then dissolved in a suitable amount of water, and the resulting solution was adjusted to pH 3.0˜3.5 to give the product 9-[(R)-2-(phosphonomethoxy)propyl]adenine (PMPA). Furthermore, dichloromethane or chloroform could be used as reaction solvent and iodotrimethylsilane or chlorotrimethylsilane/potassium iodide as the deprotection agent.

後処理

  1. temperaturethe mixture was refluxed
  2. customwas removed under vacuum
  3. dissolutionthe resultant residue was then dissolved in a suitable amount of water

出典と根拠

ORDレコード
ord-8714acba1ab1429395fcb886b63619c7
出典データセット
uspto-grants-2013_08
特許番号
US08507463B2

関連ノート

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