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Sodium Azide → [[3-[3,5-Difluoro-4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]azide

HRID 1940652
ノート
印刷プレビュー

反応式

HRID 1940652 の反応式
[F:1][C:2]1[CH:3]=[C:4]([N:22]2[CH2:26][CH:25]([CH2:27]OS(C3C=CC(C)=CC=3)(=O)=O)[O:24][C:23]2=[O:39])[CH:5]=[C:6]([F:21])[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-:40]=[N+:41]=[N-:42].[Na+].CCOC(C)=O.CCCCCC>CN(C=O)C.CCOC(C)=O>[F:21][C:6]1[CH:5]=[C:4]([N:22]2[CH2:26][CH:25]([CH2:27][N:40]=[N+:41]=[N-:42])[O:24][C:23]2=[O:39])[CH:3]=[C:2]([F:1])[C:7]=1[N:8]1[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH2:12][CH2:13]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 33557Sodium AzideHCID 21226206Ethyl acetate hexaneHCID 86749743[[3-[3,5-Difluoro-4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-p-toluenesulfonate

生成物 1

HCID 54095168[[3-[3,5-Difluoro-4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]azide収率 98.3%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

The [[3-[3,5-difluoro-4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-p-toluenesulfonate (29.661 g, 52 mmol) was dissolved in dry DMF (125 mL) and then treated with solid NaN3 (10.19 g, 156 mmol) at room temperature. The reaction was heated to 60° C. for three hours and then allowed to cool to room temperature overnight under N2. The reaction was found to he complete by TLC (30% EtOAc/hexane, run twice, UV short wave). The reaction mixture was concentrated in vacuo to give a cream colored solid. The crude product was dissolved in 600 mL EtOAc and then washed with both H2O (2×500 mL) and brine (500 mL). The aqueous portions were back-extracted with more EtOAc (2×400 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to yield 22.41 g (91%) of the title compound as a pale yellow solid with mp 115°-117° C.

後処理

  1. temperatureto cool to room temperature overnight under N2
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give a cream colored solid
  4. washwashed with both H2O (2×500 mL) and brine (500 mL)
  5. extractionThe aqueous portions were back-extracted with more EtOAc (2×400 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4e5b1e2439a9476e81ccb604e9d6a083
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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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート