反応式
[F:1][C:2]1[C:3](=[O:36])[NH:4][C:5](=[O:35])[N:6]([CH:34]=1)[C@@H:7]1[O:33][C@H:11]([CH2:12][O:13]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C@@H:9]([OH:10])[CH2:8]1.[OH-].[K+].[Br:39][C:40]1[S:41][C:42]([CH2:47]Cl)=[C:43]([Br:46])[C:44]=1[Br:45]>O1CCOCC1>[F:1][C:2]1[C:3](=[O:36])[NH:4][C:5](=[O:35])[N:6]([CH:34]=1)[C@@H:7]1[O:33][C@H:11]([CH2:12][OH:13])[C@@H:9]([O:10][CH2:47][C:42]2[S:41][C:40]([Br:39])=[C:44]([Br:45])[C:43]=2[Br:46])[CH2:8]1参加物
反応条件
- 温度
- 80 °C
実験手順
To a solution of 5.00 g of 2'-deoxy-5-fluoro-5'-O-trityluridine in 100 ml of dioxane were added 5.74 g of fine powder of potassium hydroxide and 5.65 g of 2,3,4- tribromo-5-chloromethylthiophene, and the mixture was stirred at a temperature of 80° C. for 2 hours. The reaction mixture was concentrated and the residue was dissolved in 100 ml of ethyl acetate. The solution was washed with aqueous solution of acetic acid, dried and concentrated. To the residue was added 100 ml of 80% acetic acid and the mixture was left to stand at a temperature of 80° C. for one hour. The solvent was distilled off and the residue was placed on silica gel column and eluted with 2% methanol-chloroform for purification, giving 1.07 g (18%) of the desired 2'-deoxy 5-fluoro-3'-O-(3,4,5-tribromo-2-thenyl)uridine.
後処理
- concentrationThe reaction mixture was concentrated
- dissolutionthe residue was dissolved in 100 ml of ethyl acetate
- washThe solution was washed with aqueous solution of acetic acid
- customdried
- concentrationconcentrated
- additionTo the residue was added 100 ml of 80% acetic acid
- waitthe mixture was left
- waitto stand at a temperature of 80° C. for one hour
- distillationThe solvent was distilled off
- washeluted with 2% methanol-chloroform for purification
出典と根拠
- ORDレコード
- ord-b804364ba17d4ef4a3b26b125af93c3a
- 出典データセット
- uspto-grants-1991_02
- 特許番号
- US04992534
関連ノート
読み込み中…