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
반응 조건
- 온도
- 80 °C
실험 절차
To a stirred mixture of (4S)-1,4-dihydro-2,6-dimethyl-4-(2',3'-dichorophenyl)-5-carboxymethyl-3-pyridinecarboxylic acid (2.0 g, 5.61 mmol) and sodium bicarbonate (0.96 g, 11.4 mmol) in DMF (100 ml) under nitrogen atmosphere was added chloromethyl butyrate (1.16 g, 8.5 mmol). The reaction mixture was heated at 80° C. for 23 h. Workup by filtration followed by evaporation of solvent. The crude residue was dissolved in dichloromethane and washed with sodium bicarbonatesolution. The organic phase was dried over sodium sulfate and evaporated. Recrystallization first from a mixture of 45% ethylacetate in isooctane followed by diisopropylether gave colorless crystals (1.08 g, 42%), mp. 128°-129° C. NMR spectral data are identical with the data of the racemate as shown in Example 3. [α]D20 =-21.50 (1 % in methanol).
후처리
- filtrationWorkup by filtration
- customfollowed by evaporation of solvent
- dissolutionThe crude residue was dissolved in dichloromethane
- washwashed with sodium bicarbonatesolution
- dry with materialThe organic phase was dried over sodium sulfate
- customevaporated
- customRecrystallization
- additionfirst from a mixture of 45% ethylacetate in isooctane
출처 및 근거
- ORD 기록
- ord-c9e01bd588bd470c9254e44a5f9f9efc
- 출처 데이터셋
- uspto-grants-1999_01
- 특허 번호
- US05856346
연결된 노트
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