Ethyl Acetate → (R)-4-methyl-3-pyridin-2-yl[1,2,3]oxathiazolidine-2,2-dioxide

HRID 566588

Reaction equation

HRID 566588 reaction equation
I([O-])(=O)(=O)=O.[Na+].[CH3:7][CH:8]1[CH2:12][O:11][S@@:10](=[O:13])[N:9]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(OCC)(=[O:22])C>O.C(#N)C.[Ru](Cl)(Cl)Cl>[CH3:7][C@@H:8]1[CH2:12][O:11][S:10](=[O:22])(=[O:13])[N:9]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 54573470(R)-4-methyl-3-(2-pyridyl)-[1,2,3]oxathiazolidine 2-oxide

Product 1

HCID 22863100(R)-4-methyl-3-pyridin-2-yl[1,2,3]oxathiazolidine-2,2-dioxide

Reagents, catalysts & solvents 3

HCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A solution of sodium periodate (21 g, 0.10 moles) in water (150 ml) was added slowly to a solution of (R)4-methyl-3-pyridin-2-yl-[1,2,3]oxathiazolidine-2-oxide (15.4 g, 0.78 moles) and ruthenium(III)chloride (20 mg) in acetonitrile (1540 ml) whilst the temperature was kept below 5° C. A heavy precipitate developed. The mixture was poured into a mixture of ethyl acetate (500 ml) and water (500 ml) and then shaken. The organic phase was retained and the aqueous phase was extracted with further ethyl acetate (2×500 ml). The organic phases were combined, backwashed with water (500 ml), dried (MgSO4) and then evaporated in vacuo to give (R)-4-methyl-3-(2-pyridyl)-[1,2,3]-oxathiazolidine-2,2-dioxide (15.5 g) as a yellow oil.

Workup

  1. customwas kept below 5° C
  2. extractionthe aqueous phase was extracted with further ethyl acetate (2×500 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-375eb5af7160439d8f8070615c47fc9c
Source dataset
uspto-grants-2001_01
Patent number
US06175012B1

Linked notes

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