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

HRID 895600노트

반응식

HRID 895600 반응식
[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C@@H:10]([OH:20])[C@:9]([CH3:22])(O)[C:8]=3[CH:7]=[CH:6][N:5]2[C:23]=1[CH3:24].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>COCCO>[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C@@H:10]([OH:20])[C:9](=[CH2:22])[C:8]=3[CH:7]=[CH:6][N:5]2[C:23]=1[CH3:24]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 10286525(7R,8R,9R)-2,3,7-trimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

생성물 1

HCID 20812188(8S,9R)-2,3-Dimethyl-8-hydroxy-7-methylidene-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]-naphthyridine수율 23.3%

시약·촉매·용매 1

HCID 80192-Methoxyethanol용매

실험 절차

A mixture of 1.0 g of (7R,8R,9R)-2,3,7-trimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine and 0.45 g of conc. sulfuric acid in 15 ml of 2-methoxyethanol is vigorously stirred at room temperature for 48 h, the reaction mixture is poured into 50 ml of saturated aqueous sodium hydrogencarbonate solution, extracted three times with 50 ml of dichloromethane each time, and the organic phases are combined and washed with a little water. After stripping off the solvent in vacuo, the oily residue obtained is purified on silica gel (eluent: dichloromethane/methanol 100/1). 0.22 g of the title compound is obtained as pale yellow crystals of melting point 199-202° C. (diethyl ether).

후처리

  1. extractionextracted three times with 50 ml of dichloromethane each time
  2. washwashed with a little water
  3. customthe oily residue obtained
  4. customis purified on silica gel (eluent: dichloromethane/methanol 100/1)

출처 및 근거

ORD 기록
ord-3d68ec10f05842718c163861bfcdb88f
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916825B2

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