Sodium Iodide → Methyl (S)-2-(Boc-amino)-4-iodobutanoate
Reaction equation
[CH3:1][O:2][C:3](=[O:16])[C@@H:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6]Br.[Na+].[I-:18]>CC(C)=O>[CH3:1][O:2][C:3](=[O:16])[C@@H:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6][I:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of (S)-4-bromo-2-tert-butoxycarbonylaminobutyric acid methyl ester (1.19 g, 4.0 mmol) (Example 120, Steps A-D) and NaI (6.0 g, 40.0 mmol) in acetone (25 mL) was heated to 70° C. for 2 hours. The mixture was then cooled to room temperature, concentrated under reduced pressure and partitioned between water (10 mL) and ether (40 mL). The layers were separated and the organic layer was washed with water (10 mL), dried over MgSO4, filtered through Celite, and concentrated under reduced pressure to afford 1.26 g of the product (92% yield).
Workup
- temperatureThe mixture was then cooled to room temperature
- concentrationconcentrated under reduced pressure
- custompartitioned between water (10 mL) and ether (40 mL)
- customThe layers were separated
- washthe organic layer was washed with water (10 mL)
- dry with materialdried over MgSO4
- filtrationfiltered through Celite
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-9a0fbb9f4d004c2db7ee35a934689669
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518983B2
Reaction notes
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