反応式
[CH2:1]([O:3][C:4]([C@@:6]1([NH:11][C:12]([C@@H:14]2[CH2:18][C@@H:17]([OH:19])[CH2:16][N:15]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:13])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].C(N(C(C)C)CC)(C)C.[N+:36]([C:39]1[CH:47]=[CH:46][C:42]([C:43](Cl)=[O:44])=[CH:41][CH:40]=1)([O-:38])=[O:37]>CN(C)C1C=CN=CC=1.CCOC(C)=O>[CH2:1]([O:3][C:4]([C@@:6]1([NH:11][C:12]([C@@H:14]2[CH2:18][C@@H:17]([O:19][C:43](=[O:44])[C:42]3[CH:41]=[CH:40][C:39]([N+:36]([O-:38])=[O:37])=[CH:47][CH:46]=3)[CH2:16][N:15]2[C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])=[O:13])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 2
実験手順
To a mixture of (2S,4R)-tert-butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate (90.0 g), 4-dimethylaminopyridine (1.5 g), diisopropylethylamine (39.5 g) and EtOAc (180 mL), at 5° C., was added p-nitrobenzoyl chloride (49.9 g) as a solution in EtOAc (310 mL). After 1 h at 5° C., the reaction was warmed to rt. After 15 h, the reaction was cooled to rt and additional p-nitrobenzoyl chloride (8.6 g), diisopropylethylamine (11.0 g), and EtOAc (70 mL) were added to the reaction solution. After 4.5 h at 5° C., the reaction was quenched by the addition of water (90 mL). The resulting layers were separated and the organic layer was washed with a 1.0 N aqueous solution of HCl (180 mL), 10% aqueous solution of KHCO3 (2×135 g), water (150 mL), and a 10% aqueous solution of NaCl. The product-containing organic layer was concentrated to an oil (99% yield).
後処理
- waitAfter 15 h
- temperaturethe reaction was cooled to rt
- waitAfter 4.5 h at 5° C.
- customthe reaction was quenched by the addition of water (90 mL)
- customThe resulting layers were separated
- washthe organic layer was washed with a 1.0 N aqueous solution of HCl (180 mL), 10% aqueous solution of KHCO3 (2×135 g), water (150 mL)
出典と根拠
- ORDレコード
- ord-6133c6e76e694019810dd335b913be31
- 出典データセット
- uspto-grants-2014_06
- 特許番号
- US08748374B2
関連ノート
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