Dimethylformamide → 167356-39-0

HRID 341869

反応式

HRID 341869 の反応式
[CH3:1][C:2]1[NH:3][C:4]([CH3:23])=[C:5]([CH2:19]C(O)=O)[C@@H:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=2[Cl:18])[C:7]=1[C:8]([OH:10])=[O:9].[C:24](=O)(O)[O-:25].[Na+].[C:29]([O:34][CH2:35]Cl)(=[O:33])[CH2:30][CH2:31][CH3:32].CN(C=[O:41])C>>[Cl:18][C:12]1[C:13]([Cl:17])=[CH:14][CH:15]=[CH:16][C:11]=1[C@H:6]1[C:5]([C:19]([O:25][CH3:24])=[O:41])=[C:4]([CH3:23])[NH:3][C:2]([CH3:1])=[C:7]1[C:8]([O:10][CH2:35][O:34][C:29](=[O:33])[CH2:30][CH2:31][CH3:32])=[O:9]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 2725008Chloromethyl butanoateHCID 22884797HCID 22884797、化合物

生成物 1

HCID 22884799167356-39-0収率 70%

反応条件

温度
80 °C

実験手順

To a stirred mixture of (4R)-1,4-dihydro-2,6-dimethyl-4-(2',3'-dichorophenyl)-5-carboxymethyl-3-pyridinecarboxylic acid (2.93 g, 8.23 mmol) and sodium bicarbonate (1.38 g, 16.5 mmol) in DMF (150 ml) under nitrogen atmosphere was added chloromethyl butyrate (1.72 g, 12.6 mmol). The reaction mixture was heated at 80° C. for 17 h. Workup by filtration followed by evaporation of solvent. The crude residue was chromatographed on silica gel with 5% ethyl acetate in dichloromethane. Recrystallization from diisopropylether gave colorless crystals (2.62 g, 70%), mp. 128°-129° C. NMR spectral data are identical with the data of the racemate as shown in Example 3. [α]D20 =+17.5° (1% in methanol).

後処理

  1. filtrationWorkup by filtration
  2. customfollowed by evaporation of solvent
  3. customThe crude residue was chromatographed on silica gel with 5% ethyl acetate in dichloromethane
  4. customRecrystallization from diisopropylether

出典と根拠

ORDレコード
ord-87aacaf89f584194a518128384d95ddc
出典データセット
uspto-grants-1999_01
特許番号
US05856346

関連ノート

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