반응 #1605798

ord-0d8a6a37bf284d8090deda0eada1db7f

반응 방정식

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
수율 90.0%

반응 조건

온도
65°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.STIRRINGthe mixture was stirred at the same temperature overnight
  2. 2
    workup.ADDITIONTo the reaction solution was added
  3. 3
    기타purified water
  4. 4
    workup.STIRRINGstirred at room temperature for 1 hour
  5. 5
    여과The precipitate was collected by filtration
  6. 6
    세척washed with purified water
  7. 7
    기타By drying under reduced pressure

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US09072734B2uspto-grants-2015_07