Water → HCID 131734122, compound

HRID 716157Notes

Reaction equation

HRID 716157 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1([CH3:27])[O:11][C@H:10]([C@H:12]([OH:14])[CH3:13])[C@H:9]([CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[O:8]1.C(N(CC)CC)C.O>C(OCC)(=O)C>[CH3:1][S:2]([O:14][C@@H:12]([C@H:10]1[C@H:9]([CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:18]([CH3:19])[CH3:20])[CH:21]([CH3:23])[CH3:22])[O:8][C:7]([CH3:6])([CH3:27])[O:11]1)[CH3:13])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 123462581HCID 123462581, compound

Product 1

HCID 131734122HCID 131734122, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

0.75 mL of methanesulfonyl chloride was added dropwise to a solution of 1.6 g of (1R)-1-((4R,5S)-2,2-dimethyl-5-(((tris(propan-2-yl)silyl)oxy)methyl)-1,3-dioxolane-4-yl)ethan-1-ol and 2.7 mL of triethylamine in 16 mL of ethyl acetate at a temperature of 5° C. to 10° C., and the obtained mixture was then stirred at room temperature for 10 minutes. Thereafter, ethyl acetate and water were added to the reaction mixture. The organic layer was fractionated, and it was washed with a saturated sodium chloride aqueous solution and was then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, so as to obtain 1.98 g of (1R)-1-((4R,5S)-2,2-dimethyl-5-(((tris(propan-2-yl)silyl)oxy)methyl)-1,3-dioxolane-4-yl)ethyl methanesulfonate in the form of a colorless oily product.

Workup

  1. washit was washed with a saturated sodium chloride aqueous solution
  2. dry with materialwas then dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-44ef8a0ff4184707a4377bec483de37b
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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