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Sodium Azide → (3R,5S)-5-[(S)-1-Azido-2-benzyloxyethyl]-3-methyldihydrofuran-2-one

HRID 1694955
ノート
印刷プレビュー

反応式

HRID 1694955 の反応式
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:12][CH2:13][C@@H:14](OS(C)(=O)=O)[C@@H:15]1[CH2:19][C@@H:18]([CH3:20])[C:17](=[O:21])[O:16]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN1C(=O)N(C)CCC1>[N:1]([C@H:14]([C@H:15]1[O:16][C:17](=[O:21])[C@H:18]([CH3:20])[CH2:19]1)[CH2:13][O:12][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[N+:2]=[N-:3]
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

4

反応物 2

HCID 33557Sodium AzideHCID 86636121Methanesulfonic acid (R)-2-benzyloxy-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl ester

生成物 1

HCID 45277065(3R,5S)-5-[(S)-1-Azido-2-benzyloxyethyl]-3-methyldihydrofuran-2-one収率 91.2%

試薬・触媒・溶媒 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-溶媒

反応条件

温度
60 °C

実験手順

2.93 g of sodium azide (45.1 mmol) was added to a solution of 9.90 g of methanesulfonic acid (R)-2-benzyloxy-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl ester obtained in Example (76d) (30.1 mmol) in N,N′-dimethylpropyleneurea (100 ml) at room temperature, and the mixture was stirred at 60° C. for three days. The reaction mixture was cooled and then poured into ice water, followed by extraction with diethyl ether. Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=5/1) to obtain 7.56 g of the title compound (yield: 91%).

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionfollowed by extraction with diethyl ether
  3. washThen, the organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=5/1)

出典と根拠

ORDレコード
ord-358f4446c6f54f718c4faa8c6b622c88
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08158790B2

反応ノート

読み込み中…

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