反応 #1605798

ord-0d8a6a37bf284d8090deda0eada1db7f

反応方程式

O=c1ccc2c([C@@H](O)CBr)ccc(OCc3ccccc3)c2[nH]1
8-Benzyloxy-5-((R)-2-bromo-1-hyroxyethyl)-1H-quinolin-2-one
[N-]=[N+]=[N-].[Na+]
sodium azide
[N-]=[N+]=[N-].[Na+]
Sodium azide
[N-]=[N+]=NC[C@H](O)c1ccc(OCc2ccccc2)c2[nH]c(=O)ccc12
5-((R)-2-azido-1-hyroxyethyl)-8-benzyloxy-1H-quinolin-2-one
収率 90.0%

反応条件

温度
65°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    workup.STIRRINGthe mixture was stirred at the same temperature overnight
  2. 2
    workup.ADDITIONTo the reaction solution was added
  3. 3
    その他purified water
  4. 4
    workup.STIRRINGstirred at room temperature for 1 hour
  5. 5
    ろ過The precipitate was collected by filtration
  6. 6
    洗浄washed with purified water
  7. 7
    その他By drying under reduced pressure

実験手順

8-Benzyloxy-5-((R)-2-bromo-1-hyroxyethyl)-1H-quinolin-2-one (20.8 g, 55.6 mmol) and sodium azide (3.61 g, 55.5 mmol) were suspended in N,N-dimethylformamide (100 mL) and the mixture was stirred at 65° C. for 3 hours. Sodium azide (1.81 g, 27.8 mmol) was added thereto and the mixture was stirred at the same temperature overnight. To the reaction solution was added purified water and stirred at room temperature for 1 hour. The precipitate was collected by filtration and washed with purified water. By drying under reduced pressure, 5-((R)-2-azido-1-hyroxyethyl)-8-benzyloxy-1H-quinolin-2-one (16.8 g) was obtained.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US09072734B2uspto-grants-2015_07