Sulfuric Acid → (7R,8R,9R)-2,3-Dimethyl-8-hydroxy-7-(2-hydroxyethoxy)-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

HRID 723390노트

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HRID 723390 반응식
[OH:1][C@@H:2]1[C:11]2[CH:10]=[CH:9][N:8]3[C:12]([CH3:16])=[C:13]([CH3:15])[N:14]=[C:7]3[C:6]=2[NH:5][C@H:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:3]1[OH:23].S(=O)(=O)(O)O.[OH-].[Na+].C[O:32][CH2:33][CH2:34]O>>[CH3:15][C:13]1[N:14]=[C:7]2[C:6]3[NH:5][C@H:4]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C@@H:3]([OH:23])[C@H:2]([O:1][CH2:34][CH2:33][OH:32])[C:11]=3[CH:10]=[CH:9][N:8]2[C:12]=1[CH3:16]

참가 물질

5

반응물 4

HCID 1118Sulfuric AcidHCID 80192-MethoxyethanolHCID 14798Sodium HydroxideHCID 10215014(7R,8R,9R)-2,3-dimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-h][1,7]naphthyridine

생성물 1

HCID 10193645(7R,8R,9R)-2,3-Dimethyl-8-hydroxy-7-(2-hydroxyethoxy)-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

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온도
55 °C

실험 절차

To a suspension of 2.00 g (6.40 mmol) (7R,8R,9R)-7,8-Dihydroxy-2,3-dimethyl-9-phenyl-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridine in 2-methoxyethanol (100 ml) is added 1.26 g (12.8 mmol) sulfuric acid and the mixture is stirred for 3 h at 55° C. Subsequently the reaction is poured out into a of 0° C. cooled aqueous solution of sodium hydroxide (2N). The mixture is extracted with dichloromethane two times. The combined organic layer are washed with water four times, dried over sodium sulfate and concentrated in vacuo. The crude product is purified by column chromatography (diethyl ether/2-propanol: 10/1) to give 0.35 g (0.99 mmol/16%) of the title compound as a colourless solid with a melting point of 107–109° C. (diethyl ether).

후처리

  1. additionSubsequently the reaction is poured out into a of 0° C.
  2. extractionThe mixture is extracted with dichloromethane two times
  3. washThe combined organic layer are washed with water four times
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by column chromatography (diethyl ether/2-propanol: 10/1)

출처 및 근거

ORD 기록
ord-6178727dfe674edf8d77ca2c1b17ae58
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141567B2

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