Triethylamine → rac-(2R,3S,4R,5S)-3-(3-chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2-methoxycarbonyl-2-methyl-propyl)-pyrrolidine-2-carboxylic acid tert-butyl ester
반응식
[CH3:1][O:2][C:3](=[O:18])[C:4]([CH3:17])([CH3:16])[CH2:5]/[CH:6]=[N:7]/[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[Cl:19][C:20]1[C:21]([F:38])=[C:22](/[CH:26]=[C:27](/[C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[F:37])\[C:28]#[N:29])[CH:23]=[CH:24][CH:25]=1.C(N(CC)CC)C.C1CCN2C(=NCCC2)CC1>ClCCl.C(O)(C)(C)C>[C:12]([O:11][C:9]([CH:8]1[CH:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([Cl:19])[C:21]=2[F:38])[C:27]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[F:37])([C:28]#[N:29])[CH:6]([CH2:5][C:4]([C:3]([O:2][CH3:1])=[O:18])([CH3:17])[CH3:16])[NH:7]1)=[O:10])([CH3:13])([CH3:15])[CH3:14]참가 물질
7
반응물 4
생성물 1
시약·촉매·용매 2
실험 절차
In a manner similar to the method described in Example 100b, 4-[(E)-tert-butoxycarbonylmethylimino]-2,2-dimethyl-butyric acid methyl ester prepared in Example 104a (2.1 g, 8.3 mmol) was reacted with (Z)-3-(3-chloro-2-fluoro-phenyl)-2-(4-chloro-2-fluoro-phenyl)-acrylonitrile (2.05 g, 6.7 mmol) prepared in Example 52a, AgF (1.27 g, 10 mmol), and triethylamine (2.3 mL, 17 mmol) in dichloromethane (150 mL) at room temperature for 18 h, followed by the reaction with DBU (2 ml) in tert-butanol (10 mL) at 100° C. for 2 h to give rac-(2R,3S,4R,5S)-3-(3-chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2-methoxycarbonyl-2-methyl-propyl)-pyrrolidine-2-carboxylic acid tert-butyl ester as a white solid (0.75 g, 20%).
출처 및 근거
- ORD 기록
- ord-2da40d95e7a8471cbede15282ff21f2f
- 출처 데이터셋
- uspto-grants-2013_01
- 특허 번호
- US08354444B2
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