Hydrochloric Acid → Tert-butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

HRID 1748256Notes

Reaction equation

HRID 1748256 reaction equation
[CH3:1][CH:2]1[CH:6]([CH3:7])[O:5][S:4](=[O:8])[N:3]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].I([O-])(=O)(=O)=[O:17].[Na+].Cl>C(#N)C.O>[CH3:1][CH:2]1[CH:6]([CH3:7])[O:5][S:4](=[O:17])(=[O:8])[N:3]1[C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 67234977Tert-butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2-oxide

Product 1

HCID 86682386Tert-butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxideYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2-oxide in acetonitrile (50 mL) and water (30 mL) cooled to 0° C. is added sodium periodate (6.4 g, 30.0 mmol). After 5 min, the pH of the mixture is adjusted to 7-8 by addition of saturated Na2HPO4 solution. Then the solution of RuCl3 (41.5 mg, 0.2 mmol) in water (0.5 mL) is added. The pH of the reaction mixture is kept between 6 and 9 by addition of Na2HPO4 solution. After stirring for 2 h, water (100 mL) is added and the pH is adjusted to 6 by addition of 2 M HCl solution. The mixture is extracted with EtOAc and the organic layer is separated, washed with NaHCO3 and brine. The aqueous washing layers are back extracted once with EtOAc. The combined organic layers are dried (MgSO4) and concentrated to afford the crude compound which is purified by flash column chromatography using EtOAc in hexanes to afford the title compound (4.48 g, 85% for 4 steps).

Workup

  1. extractionThe mixture is extracted with EtOAc
  2. customthe organic layer is separated
  3. washwashed with NaHCO3 and brine
  4. extractionThe aqueous washing layers are back extracted once with EtOAc
  5. dry with materialThe combined organic layers are dried (MgSO4)
  6. concentrationconcentrated
  7. customto afford the crude compound which
  8. customis purified by flash column chromatography

Sources & evidence

ORD record
ord-ff499427622f45a6bf04ff032c684aa6
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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