Hydrogen Bromide → 9-Bromonoscapine

HRID 1968413노트

반응식

[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

참가 물질

반응물 3

HCID 260Hydrogen Bromide

HCID 275196Noscapine

HCID 178514845HCID 178514845, 화합물

생성물 1

HCID 102550819-Bromonoscapine수율 82%

반응 조건

온도: 25 °C

실험 절차

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.

후처리

customTargetin was synthesized

출처 및 근거

ORD 기록: ord-889d2a73c91f4c0191ea369640bb008f
출처 데이터셋: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08426398B2

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