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

HRID 1694955
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HRID 1694955 반응식
[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]
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참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

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

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온도
60 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-358f4446c6f54f718c4faa8c6b622c88
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08158790B2

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