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

HRID 985084노트

반응식

HRID 985084 반응식
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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-95e973b9a8de40cf9f8e5dbcab535c41
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06869949B2

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