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 895600ノート

反応式

HRID 895600 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 80192-Methoxyethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3d68ec10f05842718c163861bfcdb88f
出典データセット
uspto-grants-2005_07
特許番号
US06916825B2

反応ノート

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