Sodium Azide → (3R,5S)-5-[(S)-1-Azido-2-benzyloxyethyl]-3-propyldihydrofuran-2-one
Reaction equation
[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]([CH2:20][CH2:21][CH3:22])[C:17](=[O:23])[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:23])[C@H:18]([CH2:20][CH2:21][CH3:22])[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]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
7.49 g of sodium azide (115 mmol) was added to a solution of 29.1 g of methanesulfonic acid (R)-2-benzyloxy-1-[(2S,4R)-5-oxo-4-propyltetrahydrofuran-2-yl]ethyl ester obtained in Example (116d) (81.7 mmol) in N,N′-dimethylpropyleneurea (300 ml) at room temperature, and the mixture was stirred at 60° C. for two 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 23.0 g of the title compound (yield: 93%).
Workup
- temperatureThe reaction mixture was cooled
- extractionfollowed by extraction with diethyl ether
- washThen, the organic layer was washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationAfter filtration
- customthe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=6/1)
Sources & evidence
- ORD record
- ord-60ae03f5f4bb43deab28d8ec174e3adf
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158790B2
Reaction notes
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