Dichloromethane → 2-[(4R,6S)-6-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide

HRID 445936Notes

Reaction equation

HRID 445936 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

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 866815062-[(4R,6S)-6-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide

Product 1

HCID 866815082-[(4R,6S)-6-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-[(4R,6S)-6-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide (10.0 g), dichloromethane (150.0 mL), and triethylamine (17.0 mL) were added to a reactor. Methanesulfonyl chloride (4.7 mL) was added to the reaction mixture, which was then stirred for 2 hours. Water (200.0 mL) was added to the reaction mixture under stirring. The separated organic layer was washed with 0.5N hydrochloric acid solution (100.0 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 (13 g).

Workup

  1. stirringunder stirring
  2. washThe separated organic layer was washed with 0.5N hydrochloric acid solution (100.0 mL)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6aa73dfc2f8c48c49fb6849b89e76dbd
Source dataset
uspto-grants-2013_07
Patent number
US08476432B2

Reaction notes

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