Triethylamine → Methyl (S)-2-methyl-3-((methylsulfonyl)oxy)propanoate
Reaction equation
[CH3:1][O:2][C:3](=[O:8])[C@@H:4]([CH3:7])[CH2:5][OH:6].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(OC(=O)CC(C)=O)C>ClCCl>[CH3:1][O:2][C:3](=[O:8])[C@@H:4]([CH3:7])[CH2:5][O:6][S:17]([CH3:16])(=[O:19])=[O:18]Participants
6
Procedure
3 g (25.3 mmol) of (S)-3-hydroxy-2-methyl-propionic acid methyl ester was dissolved in dichloromethane 50 mL, then 5.3 mL (37.9 mmol) of triethylamine was dropwise added thereto. Thereafter, 2.16 mL (27.9 mmol) of methanesulfonyl chloride was added to the solution at 0° C. After 1 hour, 200 mL of ethylacetoacetate was added to the solution and then the reaction solution was washed with water and then an organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, then the residue was purified by column chromatography to give 4.97 g (25.3 mmol) of the title compound in a yield of 100%.
Workup
- washthe reaction solution was washed with water
- dry with materialan organic layer was dried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-71898879b64a493db5528ec7feb6f1c2
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879848B2
Reaction notes
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