Methyl acetoacetate → methyl-(E)-7[5-(4-fluorophenyl)1,2-dihydro-7-isopropyl-2-oxo-1,8-naphthyridin-6-yl]-5-hydroxy-3-oxo-hept-6-enoate

HRID 1087049ノート

反応式

HRID 1087049 の反応式
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:32](/[CH:33]=[CH:34]/[CH:35]=[O:36])=[C:31]([CH:37]([CH3:39])[CH3:38])[N:30]=[C:29]3[C:24]=2[CH:25]=[CH:26][C:27](=[O:40])[NH:28]3)=[CH:19][CH:18]=1>O1CCCC1.CCCCCC.O.C(O)(=O)C>[CH3:8][O:7][C:1](=[O:6])[CH2:2][C:3](=[O:4])[CH2:5][CH:35]([OH:36])/[CH:34]=[CH:33]/[C:32]1[C:23]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)=[C:24]2[C:29](=[N:30][C:31]=1[CH:37]([CH3:39])[CH3:38])[NH:28][C:27](=[O:40])[CH:26]=[CH:25]2

参加物

9

反応物 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 14850559(E)-3-[5-(4-Fluorophenyl)-1,2-dihydro-7-isopropyl-2-oxo1, 8-naphthyridin-6-yl]-prop-2-enalHCID 178418339Butyllithium

生成物 1

HCID 14850560methyl-(E)-7[5-(4-fluorophenyl)1,2-dihydro-7-isopropyl-2-oxo-1,8-naphthyridin-6-yl]-5-hydroxy-3-oxo-hept-6-enoate収率 102%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒

実験手順

5.47 g (50.7 mmol) of methyl acetoacetate in 5 ml of tetrahydrofuran are added dropwise at -5° C. to 0° C. under argon to a suspension of 1.69 g (56.4 mmol) of 80% strength sodium hydride in 50 ml of anhydrous tetrahydrofuran. After 15 min, 41 ml (67.6 mmol) of 15% strength butyl lithium in hexane are added dropwise at the same temperature and, after a further 15 min, a solution of 5.68 g (16.9 mmol) of the compound from Example 5 in 150 ml of tetrahydrofuran. The mixture is stirred at room temperature for one hour, then 11.2 g of acetic acid in 120 ml of water are cautiously added dropwise and the mixture is extracted three times with ethyl acetate. The organic phases are washed with saturated sodium hydrogen carbonate and sodium chloride solution, dried over sodium sulphate and concentrated. 7.8 g of crude methyl-(E)-7[5-(4 -fluorophenyl)1,2-dihydro-7-isopropyl-2-oxo-1,8-naphthyridin-6-yl]-5-hydroxy-3-oxo-hept-6-enoate are obtained as orange oil.

後処理

  1. extractionthe mixture is extracted three times with ethyl acetate
  2. washThe organic phases are washed with saturated sodium hydrogen carbonate and sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-cd2091a2d3424ebba3eb6919e694075e
出典データセット
uspto-grants-1991_07
特許番号
US05034399

反応ノート

読み込み中…