Water → HCID 131734122, compound

HRID 1508653Notes

Reaction equation

HRID 1508653 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-4c78bcf3ec5543ef8d1018498e05b8a7
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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