Perfluoro-1-butanesulfonyl fluoride → Perfluoro-1-butanesulfonic acid 7-methoxy-1-[4-((R)-1-phenyl-ethoxy)-phthalazin-1-yl)-naphthalen-2-yl ester

HRID 1711981

反応式

HRID 1711981 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([OH:32])=[C:10]2[C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][C@@H:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])=[N:15][N:14]=2)=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[F:42][C:43]([F:58])([S:54](F)(=[O:56])=[O:55])[C:44]([F:53])([F:52])[C:45]([F:51])([F:50])[C:46]([F:49])([F:48])[F:47]>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([O:32][S:54]([C:43]([F:42])([F:58])[C:44]([F:52])([F:53])[C:45]([F:50])([F:51])[C:46]([F:49])([F:48])[F:47])(=[O:56])=[O:55])=[C:10]2[C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][C@@H:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])=[N:15][N:14]=2)=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 81531DiisopropylethylamineHCID 1363525037-Methoxy-1-[4-((R)-1-phenyl-ethoxy)-phthalazin-1-yl]-naphthalen-2-ol

生成物 1

HCID 86602155Perfluoro-1-butanesulfonic acid 7-methoxy-1-[4-((R)-1-phenyl-ethoxy)-phthalazin-1-yl)-naphthalen-2-yl ester収率 83.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
23 °C

実験手順

A solution of 7-methoxy-1-[4-((R)-1-phenyl-ethoxy)-phthalazin-1-yl]-naphthalen-2-ol (1.0 g, 2.4 mmol) in diisopropylethylamine (0.94 ml, 7.1 mmol) and dichloromethane (35 ml) was treated with N,N-dimethylaminopyridine (DMAP, 50 mg, 0.41 mmol) at 0° C. Then perfluoro-1-butanesulfonyl fluoride (0.51 ml, 2.8 mmol) was added dropwise and the resulting solution was stirred for 19 hrs at 23° C. The resulting solution was quenched with sat. aqueous ammonium chloride solution. The organic layer was separated and the water layer was extracted twice with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (hexane/EtOAc 3:1) to give 1.4 g (2.0 mmol) of the title compound as an oil.

後処理

  1. customThe resulting solution was quenched with sat. aqueous ammonium chloride solution
  2. customThe organic layer was separated
  3. extractionthe water layer was extracted twice with dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (hexane/EtOAc 3:1)

出典と根拠

ORDレコード
ord-7d724ff8c31f48fe9d5c48914b96e1c2
出典データセット
uspto-grants-2010_09
特許番号
US07790882B2

関連ノート

読み込み中…