Hydrogen Bromide → 9-Bromonoscapine

HRID 1968413

反応式

HRID 1968413 の反応式
[CH3:1][N:2]1[C@@H:11]([C@H:12]2[O:21][C:19](=[O:20])[C:18]3[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=[CH:14][C:13]2=3)[C:10]2[C:9]([O:26][CH3:27])=[C:8]3[O:28][CH2:29][O:30][C:7]3=[CH:6][C:5]=2[CH2:4][CH2:3]1.[BrH:31].O.[Br]>>[CH3:1][N:2]1[C@@H:11]([C@H:12]2[O:21][C:19](=[O:20])[C:18]3[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=[CH:14][C:13]2=3)[C:10]2[C:9]([O:26][CH3:27])=[C:8]3[O:28][CH2:29][O:30][C:7]3=[C:6]([Br:31])[C:5]=2[CH2:4][CH2:3]1

参加物

4

反応物 3

HCID 260Hydrogen BromideHCID 275196NoscapineHCID 178514845HCID 178514845、化合物

生成物 1

HCID 102550819-Bromonoscapine収率 82%

反応条件

温度
25 °C

実験手順

Targetin was synthesized using a four-step synthetic scheme, as illustrated below. Noscapine (1) was brominated by adding 48% hydrobromic acid and freshly prepared bromine water. The reaction mixture was stirred for 1 hr at 25° C., and basified to pH 10 to yield 9-bromonoscapine (2) in ˜82% yield. Refluxing compound 2 in dimethyl formamide with sodium azide and sodium iodide for 15 hrs gave the corresponding azido derivative (3), which when reduced with tin chloride in the presence of thiophenol and triethylamine in tetrahydrofuran for 2 hrs at 25° C. to provide 9-aminonoscapine (4) in ˜83% yield.

後処理

  1. customTargetin was synthesized

出典と根拠

ORDレコード
ord-889d2a73c91f4c0191ea369640bb008f
出典データセット
uspto-grants-2013_04
特許番号
US08426398B2

関連ノート

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