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

HRID 1694885ノート

反応式

HRID 1694885 の反応式
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:12][CH2:13][C@H:14]([C@H:16]1[O:20][C:19](=[O:21])[C@H:18]([CH:22]([CH3:24])[CH3:23])[CH2:17]1)Br)[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:16]1[O:20][C:19](=[O:21])[C@H:18]([CH:22]([CH3:24])[CH3:23])[CH2:17]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

4

反応物 2

HCID 33557Sodium AzideHCID 66645516(3S,5S)-5-[(1R)-2-Benzyloxy-1-bromoethyl]-3-isopropyldihydrofuran-2-one

生成物 1

HCID 54578739(3S,5S)-5-[(S)-1-Azido-2-benzyloxyethyl]-3-isopropyldihydrofuran-2-one収率 51.4%

試薬・触媒・溶媒 1

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

反応条件

温度
40 °C

実験手順

5.10 g of sodium azide (78.5 mmol) was added to a solution of 22.33 g of (3S,5S)-5-[(1R)-2-benzyloxy-1-bromoethyl]-3-isopropyldihydrofuran-2-one obtained in Example (1d) (65.4 mmol) in N,N′-dimethylpropyleneurea (130 ml) at room temperature, and the mixture was stirred at 40° 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=6/1) to obtain 10.19 g of the title compound (yield: 51%).

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=6/1)

出典と根拠

ORDレコード
ord-94aca53dc13a447c857faf9c558ba6ed
出典データセット
uspto-grants-2012_04
特許番号
US08158790B2

反応ノート

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