Dimethylformamide → 167356-39-0

HRID 341869

반응식

HRID 341869 반응식
[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]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 2725008Chloromethyl butanoateHCID 22884797HCID 22884797, 화합물

생성물 1

HCID 22884799167356-39-0수율 70%

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-87aacaf89f584194a518128384d95ddc
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856346

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