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Diethyl Ether → (1R,2R,3R,5R,6R)-2,3-diazido-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

HRID 130505
ノート
印刷プレビュー

反応式

HRID 130505 の反応式
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:7][C:8]([C@:10]1([N:30]=[N+:31]=[N-:32])[C@@H:15](OS(C(F)(F)F)(=O)=O)[CH2:14][C@@H:13]2[C@H:11]1[C@@:12]2([F:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:9])[CH3:6].C(OCC)C>CN(C)C=O>[CH2:5]([O:7][C:8]([C@:10]1([N:30]=[N+:31]=[N-:32])[C@H:15]([N:1]=[N+:2]=[N-:3])[CH2:14][C@@H:13]2[C@H:11]1[C@@:12]2([F:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:9])[CH3:6]
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 3

HCID 3283Diethyl EtherHCID 33557Sodium AzideHCID 86606013(1R,2R,3S,5R,6R)-2-azido-6-fluoro-3-trifluoromethanesulfonyloxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

生成物 1

HCID 86606016(1R,2R,3R,5R,6R)-2,3-diazido-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester収率 93%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

56 mg of sodium azide was added to 250 mg of (1R,2R,3S,5R,6R)-2-azido-6-fluoro-3-trifluoromethanesulfonyloxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester dissolved in 5 mL of N,N-dimethylformamide, and the mixture was stirred for 30 minutes at room temperature. After 100 mL of diethyl ether was added to the reaction solution, this ether solution was washed four times with water and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure The residue was purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=10:1), thereby yielding 175 mg of (1R,2R,3R,5R,6R)-2,3-diazido-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester.

後処理

  1. washthis ether solution was washed four times with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe desiccant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure The residue
  5. customwas purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-835e07805f1043e5b45ac530cbcfd493
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07381746B2

反応ノート

読み込み中…

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