Hydrochloric Acid → Tert-butyl 6-methyl-1,2,3-oxathiazinane-3-carboxylate 2,2-dioxide

HRID 1521707Notes

Reaction equation

HRID 1521707 reaction equation
[CH3:1][CH:2]1[O:7][S:6](=[O:8])[N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH2:3]1.I([O-])(=O)(=O)=[O:17].[Na+].Cl>C(#N)C.O>[CH3:1][CH:2]1[O:7][S:6](=[O:17])(=[O:8])[N:5]([C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 67235111Tert-butyl 6-methyl-1,2,3-oxathiazinane-3-carboxylate 2-oxide

Product 1

HCID 86682388Tert-butyl 6-methyl-1,2,3-oxathiazinane-3-carboxylate 2,2-dioxideYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent

Procedure

The crude tert-butyl 6-methyl-1,2,3-oxathiazinane-3-carboxylate 2-oxide (2.52 g, 10.7 mmol) is dissolved in acetonitrile (25 mL) and H2O (15 mL) is added. The solution is cooled in an ice bath and sodium periodate (3.4 g, 16.1 mmol) is added in one portion. After 5 min, the pH is adjusted to 7-8 by addition of saturated Na2HPO4 solution. Then RuCl3 (22 mg, 0.11 mmol) in H2O (0.5 mL) is added. The pH is kept between 6 and 9 by addition of Na2HPO4 solution. After 2 h, H2O (100 mL) is added and pH is adjusted to 6 by addition of 2M HCl solution. The reaction mixture is extracted with EtOAc and the organic layer is washed with NaHCO3 and brine and the washes are back extracted once with EtOAc. The combined organic layers are dried (MgSO4), filtered and concentrated. The crude product is purified via by flash column chromatography using a gradient elution of 5-80% ethyl acetate/hexanes which affords the title compound (1.63 g, 61%).

Workup

  1. temperatureThe solution is cooled in an ice bath
  2. waitAfter 2 h
  3. extractionThe reaction mixture is extracted with EtOAc
  4. washthe organic layer is washed with NaHCO3 and brine
  5. extractionthe washes are back extracted once with EtOAc
  6. dry with materialThe combined organic layers are dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified via by flash column chromatography
  10. washa gradient elution of 5-80% ethyl acetate/hexanes which

Sources & evidence

ORD record
ord-cacac27ea98540c88cba1e3deed6a078
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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