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Ethyl Acetate → Methanesulfonic acid (4S,5S)-5-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-YL)-methanesulfonyloxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

HRID 1268708
Notes
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Reaction equation

HRID 1268708 reaction equation
[CH3:1][C:2]1([CH3:18])[O:6][C@@H:5]([C@@H:7]([C@@H:9]2[C@H:13]([CH2:14][OH:15])[O:12][C:11]([CH3:17])([CH3:16])[O:10]2)[OH:8])[CH2:4][O:3]1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>ClCCl.N1C=CC=CC=1>[CH3:1][C:2]1([CH3:18])[O:6][C@@H:5]([C@H:7]([O:8][S:20]([CH3:19])(=[O:22])=[O:21])[C@@H:9]2[C@H:13]([CH2:14][O:15][S:20]([CH3:19])(=[O:22])=[O:21])[O:12][C:11]([CH3:17])([CH3:16])[O:10]2)[CH2:4][O:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 13963403HCID 13963403, compound

Product 1

HCID 11026162Methanesulfonic acid (4S,5S)-5-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-YL)-methanesulfonyloxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4.1 g (0.016 mol) of {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4R,5S)-(5-hydroxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)-methanol from the aforementioned Experimental Example 2 were dissolved in a mixed solvent of 1.0 L dichloromethane and 25 mL pyridine. After cooling the mixture to 0° C., 18 mL (0.236 mol) of methanesulfonyl chloride were added and the resulting solution was stirred for 5 h at 0° C. Saturated sodium bicarbonate solution was added and the compound was extracted with chloroform. The extract was dried, filtered, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography using the eluant hexane:ethyl acetate=2:1 to obtain 6.4 g (yield: 98%) of methanesulfonic acid {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4S,5S)-(5-methanesulfonyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)methyl ester as an oil.

Workup

  1. extractionthe compound was extracted with chloroform
  2. customThe extract was dried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-68f747b8e65f449a8471b0a58b2e9cfe
Source dataset
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07199127B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes