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

HRID 1748268Notes

Reaction equation

HRID 1748268 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

To a solution of tert-butyl 6-methyl-1,2,3-oxathiazinane-3-carboxylate 2-oxide (2.52 g, 10.7 mmol) in acetonitrile (25 mL) and water (15 mL) cooled to 0° C. is added sodium periodate (3.4 g, 16.1 mmol) in one portion. After 5 min, the pH is adjusted to 7-8 by addition of saturated Na2HPO4 solution. A solution of RuCl3 (22 mg, 0.11 mmol) in water (0.5 mL) is added and the pH is kept between 6 and 9 by addition of Na2HPO4 solution. After 2 h, water (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. Then the combined organic layers are dried (MgSO4), filtered and concentrated. The crude compound is purified by flash column chromatography to afford the title compound (1.63 g, 61%).

Workup

  1. waitAfter 2 h
  2. extractionThe reaction mixture is extracted with EtOAc
  3. washthe organic layer is washed with NaHCO3 and brine
  4. extractionthe washes are back-extracted once with EtOAc
  5. dry with materialThen the combined organic layers are dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude compound is purified by flash column chromatography

Sources & evidence

ORD record
ord-7cefcda672624f0bb30f3100651ace00
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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