Acetic Acid → HCID 86587413、化合物
反応式
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@@H:6]1Br)(=O)C.O[Li].O.[CH3:28][N:29]1[C@@H:45]2[CH2:46][C:34]3=[CH:35][CH:36]=[C:37]([OH:48])[C:38]4[O:39][C@H:40]5[C@@H:41]([OH:47])[CH2:42][CH2:43][C@@H:44]2[C@:32]5([C:33]=43)[CH2:31][CH2:30]1.C(O)(=O)C>CO.O.C(Cl)(Cl)Cl>[C@@H:6]1([O:48][C:37]2[CH2:36][CH2:35][C:34]3[CH2:46][C@H:45]4[N:29]([CH3:28])[CH2:30][CH2:31][C@:32]56[C:33]=3[C:38]=2[O:39][C@H:40]5[C@@H:41]([OH:47])[CH:42]=[CH:43][C@@H:44]46)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]参加物
実験手順
2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl bromide (1.20 g, 3.0 mmol) was added in one portion to a stirred solution of LiOH·H2O (0.15 g, 3.5 mmol) and dihydromorphine (1.0 g, 3.0 mmol) in dry methanol (10 mL) at room temperature. The resulting mixture was stirred for 1 hr, a solution of LiOH·H2O (0.42 g, 10.0 mmol) in water (10 mL) was added dropwise to the mixture, and the mixture allowed to stir for an additional 3 hr. The resulting suspension was acidified to pH 7 with acetic acid (0.5 mL) and 20 mL of chloroform was added. The resulting precipitate was removed by filtration and washed with ethanol (20 mL) following by acetone (20 mL), to provide a crude product. The crude product was dissolved in 50% aqueous methanol (12 mL), recrystallized at 0° C., filtered, and dried under reduced pressure (10 mm Hg, 50° C.) to provide 0.33 g (30%) of 3-O—β-glucosyldihydromorphine.
後処理
- stirringto stir for an additional 3 hr
- additionwas added
- customThe resulting precipitate was removed by filtration
- washwashed with ethanol (20 mL)
- customto provide a crude product
- customrecrystallized at 0° C.
- filtrationfiltered
- customdried under reduced pressure (10 mm Hg, 50° C.)
出典と根拠
- ORDレコード
- ord-fb52ed6be360422dbc1d459070adaae1
- 出典データセット
- uspto-grants-2004_05
- 特許番号
- US06740641B2
反応ノート
読み込み中…