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

HRID 1934369ノート

反応式

HRID 1934369 の反応式
[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.[CH3:29][S:30][CH2:31][CH2:32]O.[OH-].[Na+]>O1CCOCC1.CN(C)C=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][CH2:32][CH2:31][S:30][CH3:29])[C:11]=3[CH:10]=[CH:9][N:8]2[C:12]=1[CH3:16]

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 789252-(Methylthio)ethanolHCID 10215014(7R,8R,9R)-2,3-dimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-h][1,7]naphthyridine

生成物 1

HCID 9929931(7R,8R,9R)-2,3-dimethyl-8-hydroxy-7-(2-methylthioethyloxy)-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 312751,4-Dioxane溶媒

実験手順

1 g of (7R,8R,9R)-7,8-dihydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine, dissolved in 30 ml of dioxane and 5 ml of dimethyl-formamide, is admixed with 0.63 g of concentrated sulfuric acid and 1 g of 2-methylmercaptoethanol. The mixture is stirred at RT for 3 h, poured into ice-water (200 ml), adjusted to pH 8 using 2 N aqueous sodium hydroxide solution and extracted three times with methylene chloride. The solvent is stripped off under reduced pressure and the oily residue that remains is purified on silica gel (mobile phase: diethyl ether). This gives 80 mg of the title compound of m.p. 118-9° C. (diisopropyl ether).

後処理

  1. extractionextracted three times with methylene chloride
  2. customthe oily residue that remains is purified on silica gel (mobile phase: diethyl ether)

出典と根拠

ORDレコード
ord-e085237b4e2d4c689ec06e95e47285e4
出典データセット
uspto-grants-2002_05
特許番号
US06384048B1

反応ノート

読み込み中…