Bromotrimethylsilane → Tenofovir

HRID 1890236

반응식

HRID 1890236 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 464205Tenofovir

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-8714acba1ab1429395fcb886b63619c7
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507463B2

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