تفاعل #1605798

ord-0d8a6a37bf284d8090deda0eada1db7f

معادلة التفاعل

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
المردود 90.0%

المذيبات

ظروف التفاعل

درجة الحرارة
65°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09072734B2uspto-grants-2015_07