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Sodium Azide → 3-[3-Fluoro-4-(4-tert-butoxycarbonylpiperazin-1-yl)phenyl]-5-azidomethyl-2-oxazolidinone

HRID 1940644
ノート
印刷プレビュー

反応式

HRID 1940644 の反応式
[F:1][C:2]1[CH:3]=[C:4]([N:21]2[CH2:25][CH:24]([CH2:26]OS(C)(=O)=O)[O:23][C:22]2=[O:32])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.[N-:33]=[N+:34]=[N-:35].[Na+]>CC(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([N:21]2[CH2:25][CH:24]([CH2:26][N:33]=[N+:34]=[N-:35])[O:23][C:22]2=[O:32])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH2:10][CH2:9]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 33557Sodium Azide3 回HCID 214626263-[3-Fluoro-4-(4-tert-butoxycarbonylpiperazin-1-yl)phenyl]-5-methanesulfonyloxymethyl-2-oxazolidinone

生成物 1

HCID 214626343-[3-Fluoro-4-(4-tert-butoxycarbonylpiperazin-1-yl)phenyl]-5-azidomethyl-2-oxazolidinone収率 92%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water
溶媒
4 回

実験手順

A solution of 440 mg (0.93 mmol) of mesylate 10 in 22 mL acetone was treated with a solution of 604 mg (9.29 mmol) of sodium azide in 6.4 mL water. The mixture was warmed at reflux for 18 hours. The mixture was cooled and a solution of 600 mg of sodium azide in 6 mL water was added followed by warming at reflux for an additional 18 hours. The mixture was cooled and a solution of 1.2 g of sodium azide in 12 mL water was added followed by warming at reflux for 24 hours. The mixture was cooled and diluted with 60 mL water and extracted with ethyl acetate (3×75). The combined organic layers were extracted with 100 mL saturated NaCl solution followed by drying (Na2SO4). Concentration in vacuo afforded 358 mg (92%) of azide 11 as a white solid, mp=130.5° C.-132.5° C., sufficiently pure for use in the next step.

後処理

  1. temperatureThe mixture was warmed
  2. temperatureat reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. temperatureby warming
  5. temperatureat reflux for an additional 18 hours
  6. temperatureThe mixture was cooled
  7. temperatureby warming
  8. temperatureat reflux for 24 hours
  9. temperatureThe mixture was cooled
  10. extractionextracted with ethyl acetate (3×75)
  11. extractionThe combined organic layers were extracted with 100 mL saturated NaCl solution
  12. dry with materialby drying (Na2SO4)
  13. concentrationConcentration in vacuo

出典と根拠

ORDレコード
ord-498d9cb7e79c4282853a240a95710bb0
出典データセット
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05700799

反応ノート

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