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

HRID 1521712Notes

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

Conditions

Temperature: 0 °C

Procedure

tert-Butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2-oxide (4.7 g, 20.0 mmol) is dissolved in acetonitrile (50 mL) and H2O (30 mL) is added. The reaction mixture is cooled to 0° C. and sodium periodate (6.4 g, 30.0 mmol) is added. After 5 min, the pH of the mixture is adjusted to 7-8 by addition of saturated Na2HPO4 solution. Then the solution of RuCl3 (42 mg, 0.2 mmol) in H2O (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, H2O (100 mL) is added and the pH is adjusted to 6 by addition of 2M HCl solution. The mixture is extracted with EtOAc and the organic layer is separated, washed with NaHCO3 and brine. The aqueous layers are back extracted once with EtOAc. Then all organic layers are combined, dried (MgSO4) and concentrated. Purification by flash column chromatography using a gradient elution of 5-80% ethyl acetate/hexanes affords the title compound (4.48 g, 89%).

Workup

extractionThe mixture is extracted with EtOAc
customthe organic layer is separated
washwashed with NaHCO3 and brine
extractionThe aqueous layers are back extracted once with EtOAc
dry with materialdried (MgSO4)
concentrationconcentrated
customPurification by flash column chromatography
washa gradient elution of 5-80% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-5a054b46e1de445ab52707ba1827944a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073926B2

Reaction notes

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