Hydrochloric Acid → (8R,9R)-8-Hydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

HRID 985084ノート

反応式

HRID 985084 の反応式
Cl.[Si]([O:9][C@H:10]1[C:19](=[O:20])[C:18]2[CH:17]=[CH:16][N:15]3[CH:21]=[C:22]([CH3:24])[N:23]=[C:14]3[C:13]=2[NH:12][C@@H:11]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(C(C)(C)C)(C)C.[OH-].[Na+]>CO>[OH:9][C@H:10]1[C:19](=[O:20])[C:18]2[CH:17]=[CH:16][N:15]3[CH:21]=[C:22]([CH3:24])[N:23]=[C:14]3[C:13]=2[NH:12][C@@H:11]1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20767689(8R,9R)-8-(tert-butyldimethylsilanyloxy)-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

生成物 1

HCID 69586463(8R,9R)-8-Hydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

30 ml of concentrated hydrochloric acid are added dropwise at room temperature in the course of 20 minutes to 29.8g (73.1 mmol) of (8R,9R)-8-(tert-butyldimethylsilanyloxy)-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one, dissolved in 30 ml of methanol. The mixture is stirred for a further 30 minutes at room temperature. The methanol is stripped off and the pH of the remaining solution is adjusted to 10 using 2M sodium hydroxide solution. The mixture is extracted three times with 30 ml of dichloromethane each time, the combined dichloromethane phases are washed once with 30 ml of water and the organic phase is dried over magnesium sulfate. The drying agent is filtered off, the filtrate is concentrated and the residue is brought to crystallization using diethyl ether. The crystallizate is filtered off with suction and dried in vacuo at 50° C. 12.2 g (57% of theory) of the title compound are obtained.

後処理

  1. extractionThe mixture is extracted three times with 30 ml of dichloromethane each time
  2. washthe combined dichloromethane phases are washed once with 30 ml of water
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationThe drying agent is filtered off
  5. concentrationthe filtrate is concentrated
  6. customthe residue is brought to crystallization
  7. filtrationThe crystallizate is filtered off with suction
  8. customdried in vacuo at 50° C

出典と根拠

ORDレコード
ord-95e973b9a8de40cf9f8e5dbcab535c41
出典データセット
uspto-grants-2005_03
特許番号
US06869949B2

反応ノート

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