Dichloromethane → 2-[(4R,6S)-6-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide
Reaction equation
[OH:1][CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])[CH2:4]1.ClCCl.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>O>[CH3:28][S:29]([O:1][CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])[CH2:4]1)(=[O:31])=[O:30]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
2-[(4R,6S)-6-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide (100.0 g), dichloromethane (800.0 mL), and triethylamine (160.6 mL) were added to a reactor. The reaction mixture was then cooled to 0˜5° C. and then methanesulfonyl chloride (44.6 mL) was added thereto, while maintaining the temperature of 0˜10° C. The reaction mixture was stirred at the same temperature for 2 hours and then water (500.0 mL) was added thereto. The separated organic layer was washed with 0.5N hydrochloric acid solution (300.0 mL) and then concentrated under reduced pressure to obtain 2-[(4R,6S)-6-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide (131 g).
Workup
- temperatureThe reaction mixture was then cooled to 0˜5° C.
- temperaturewhile maintaining the temperature of 0˜10° C
- washThe separated organic layer was washed with 0.5N hydrochloric acid solution (300.0 mL)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f5d53dbfd8c6442e9af8ffdb07952e67
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476432B2
Reaction notes
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