Acetic Acid → Methyl (E)-7-[1-butyl-5-(4-fluorophenyl)-7-isopropyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrido(2,3-d)pyrimidin-6-yl]-5-hydroxy-3-oxo-hept-6-enoate

HRID 1461349ノート

反応式

HRID 1461349 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.[CH2:16]([N:20]1[C:25]2[N:26]=[C:27]([CH:41]([CH3:43])[CH3:42])[C:28](/[CH:37]=[CH:38]/[CH:39]=[O:40])=[C:29]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[C:24]=2[C:23](=[O:44])[NH:22][C:21]1=[O:45])[CH2:17][CH2:18][CH3:19].C(O)(=O)C>O1CCCC1.CCCCCC.O>[CH2:16]([N:20]1[C:25]2[N:26]=[C:27]([CH:41]([CH3:42])[CH3:43])[C:28](/[CH:37]=[CH:38]/[CH:39]([OH:40])[CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH3:8])=[O:6])=[C:29]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[C:24]=2[C:23](=[O:44])[NH:22][C:21]1=[O:45])[CH2:17][CH2:18][CH3:19]

参加物

9

反応物 5

HCID 176Acetic AcidHCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 19980383(E)-3-[1-Butyl-5-(4-fluorophenyl)-7-isopropyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrido(2,3-d)pyrimidin-6-yl]prop-2-enalHCID 178418339Butyllithium

生成物 1

HCID 67836864Methyl (E)-7-[1-butyl-5-(4-fluorophenyl)-7-isopropyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrido(2,3-d)pyrimidin-6-yl]-5-hydroxy-3-oxo-hept-6-enoate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

0.7 g (6 mmol) of methyl acetoacetate are added dropwise at 0°-5° C. to a suspension of 0.2 g (6.6 mmol) of 80% strength sodium hydride in 8 ml of anhydrous tetrahydrofuran. After 15 min, 4.9 ml (8 mmol) of 15% strength butyllithium in hexane are added dropwise in the course of 10 min and the mixture is kept at 0° C. for a further 15 min. 0.82 g (2 mmol) of the compound from Example 6 and 10 ml of tetrahydrofuran are then added and the mixture is stirred at 0°-5° C. for 1 h. 1.2 g (20 mmol) of acetic acid in 20 ml of water are then added cautiously, the mixture is extracted three times with ethyl acetate, and the organic phase is washed with sodium chloride solution, dried over sodium sulphate and concentrated in vacuo. The residue is chromatographed on 40 g of 230-400 mesh silica gel (φ 3 cm) using petroleum/ethyl acetate (2:1) to (1:3).

後処理

  1. waitthe mixture is kept at 0° C. for a further 15 min
  2. extractionthe mixture is extracted three times with ethyl acetate
  3. washthe organic phase is washed with sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on 40 g of 230-400 mesh silica gel (φ 3 cm)

出典と根拠

ORDレコード
ord-196c739466dd460c9e0715bcb0aaa277
出典データセット
uspto-grants-1991_12
特許番号
US05075311

反応ノート

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