Sodium periodate → (s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

HRID 1521722Notes

Reaction equation

HRID 1521722 reaction equation
[CH3:1][C@@H:2]1[O:6][S:5](=[O:7])[N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.I([O-])(=O)(=O)=[O:16].[Na+]>C(#N)C.O.C(OCC)(=O)C>[CH3:1][C@@H:2]1[O:6][S:5](=[O:16])(=[O:7])[N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3]1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 67235604tert-butyl (5S)-5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2-oxide

Product 1

HCID 11195739(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxideYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (5S)-5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2-oxide (5.7 g, 25.8 mmol) in acetonitrile (60 mL) and H2O (30 mL) is added sodium periodate (8.3 g, 38.7 mmol). After 5 min, a few crystals of RuCl3 are added. The reaction is stirred for 3 hours and the resulting thick slurry is diluted with H2O (100 mL) and ethyl acetate (20 mL) and passed through a bed of Celite, rinsing with additional EtOAc. The filtrate is concentrated to remove the organic solvents and the resulting solid is isolated by filtration to afford the title compound (6.0 g, 97%).

Workup

  1. washrinsing with additional EtOAc
  2. concentrationThe filtrate is concentrated
  3. customto remove the organic solvents
  4. customthe resulting solid is isolated by filtration

Sources & evidence

ORD record
ord-7a7be4789e594388ab86630027b6e192
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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