Water → {(4S,5S)-5-[(Benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl methanesulfonate

HRID 1695018Notes

Reaction equation

HRID 1695018 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:13][CH2:14][C@@H:15]1[O:19][C:18]([CH3:21])([CH3:20])[O:17][C@H:16]1[CH2:22][OH:23])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:1][S:2]([O:23][CH2:22][C@H:16]1[C@H:15]([CH2:14][O:13][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:19][C:18]([CH3:20])([CH3:21])[O:17]1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10901124{(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol2×

Product 1

HCID 14731143{(4S,5S)-5-[(Benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl methanesulfonateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 19.21 g of methanesulfonyl chloride (168 mmol) in methylene chloride (90 ml) was added to a solution of 35.27 g of {(4S,5S)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol obtained in Reference Example (1a) (140 mmol) and 29.2 ml of triethylamine (210 mmol) in methylene chloride (270 ml) under ice-cooling over 30 minutes, and the mixture was stirred at the same temperature for 20 minutes. 0.76 ml of water (42 mmol) was added to the reaction mixture, and the mixture was further stirred at room temperature for 15 minutes. The reaction mixture was concentrated under reduced pressure and diluted with water, followed by extraction with ethyl acetate. Then, the organic layer was washed with water, a saturated sodium bicarbonate aqueous solution and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain 46.19 g of the crude title compound.

Workup

  1. temperaturecooling over 30 minutes
  2. stirringthe mixture was further stirred at room temperature for 15 minutes
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiondiluted with water
  5. extractionfollowed by extraction with ethyl acetate
  6. washThen, the organic layer was washed with water
  7. dry with materiala saturated sodium bicarbonate aqueous solution and brine and dried over anhydrous magnesium sulfate
  8. filtrationAfter filtration
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-582079029d8448fba811e2f9eb6f4fff
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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