Methanol → N-[1-[(2R,4S,5R)-4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide

HRID 1488550

反応式

HRID 1488550 の反応式
[C:1]([NH:9][C:10]1[CH:23]=[CH:22][N:13]([C@@H:14]2[O:21][C@H:18]([CH2:19][OH:20])[C@@H:16]([OH:17])[CH2:15]2)[C:12](=[O:24])[N:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:31](Cl)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CO>C(Cl)Cl>[C:31]([O:20][CH2:19][C@H:18]1[O:21][C@@H:14]([N:13]2[CH:22]=[CH:23][C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:11][C:12]2=[O:24])[CH2:15][C@@H:16]1[OH:17])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

参加物

6

反応物 4

HCID 887MethanolHCID 1049PyridineHCID 6456Trityl chlorideHCID 9797617N4-Benzoyl-2'-deoxycytidine

生成物 1

HCID 494349N-[1-[(2R,4S,5R)-4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide収率 26%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

3.31 g (10 mmol) of N-benzoyl-2'-deoxycytidine were added to 25 ml of pyridine, and then 3.07 g (11 mmol) of trityl chloride were added to the suspension. The resulting suspension was stirred at 100° C. for 1 hour, after which it was allowed to cool to room temperature. The pyridine was then removed by distillation under reduced pressure. The resulting residue was dissolved in a mixture of ethyl acetate and a saturated aqueous solution of sodium chloride. The organic layer was separated and washed twice, each time with a saturated aqueous solution of sodium chloride. The solution was then dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel (Lober column Si-60, Size C) using a gradient elution method, with mixtures of methanol and methylene chloride ranging from 2:98 to 5:95 by volume as the eluent, to give 1.47 g (yield 26%) of the title compound.

後処理

  1. temperatureto cool to room temperature
  2. customThe pyridine was then removed by distillation under reduced pressure
  3. dissolutionThe resulting residue was dissolved in a mixture of ethyl acetate
  4. customThe organic layer was separated
  5. washwashed twice
  6. dry with materialThe solution was then dried over anhydrous magnesium sulfate
  7. customafter which the solvent was removed by distillation under reduced pressure
  8. customThe resulting residue was purified by column chromatography through silica gel (Lober column Si-60, Size C)
  9. washa gradient elution method

出典と根拠

ORDレコード
ord-97ab072974a24bf8a72f463fde61becc
出典データセット
uspto-grants-1997_10
特許番号
US05674856

関連ノート

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