Hydrochloric Acid → (R)-6-(4-fluoro-3-methylbenzyloxy)-2-azidohexanoic acid
Reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]([N:28]=[N+:29]=[N-:30])[C:13](N2[C@H](CC3C=CC=CC=3)COC2=O)=[O:14])=[CH:4][C:3]=1[CH3:33].OO.[Li+].[OH-].[O-:38]S([O-])=O.[Na+].[Na+].Cl>C1COCC1.O.O>[F:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]([N:28]=[N+:29]=[N-:30])[C:13]([OH:14])=[O:38])=[CH:4][C:3]=1[CH3:33]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (0° C.) solution of (R)-3-((R)-6-(4-fluoro-3-methylbenzyloxy)-2-azidohexanoyl)-4-benzyloxazolidin-2-one (0.251 g, 0.552 mmol) in 11 mL of THF/H2O (8:3), were added stepwise 30% H2O2 (0.22 mL, 2.208 mmol) and LiOH (0.046 g, 1.105 mmol). The reaction mixture was stirred at 0° C. for 1 h then room temperature for overnight. Then a solution of Na2SO3 (0.304 g, 2.412 mmol) in 3 mL of water was added. After stirred at room temperature for 10 min, the reaction mixture was acidified with 4N HCl to pH=2 and extracted with dichloromethane (30 mL×3). The combined organic extracts dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was used directly in the next step without further purification (0.163 g, >99% yield).
Workup
- waitroom temperature for overnight
- stirringAfter stirred at room temperature for 10 min
- extractionextracted with dichloromethane (30 mL×3)
- dry with materialThe combined organic extracts dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was used directly in the next step without further purification (0.163 g, >99% yield)
Sources & evidence
- ORD record
- ord-3ebb16f8b42546a0845e06af34bf9936
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242174B2
Reaction notes
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