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

HRID 1748247Notes

Reaction equation

HRID 1748247 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 water (30 mL) is added sodium periodate (8.3 g, 38.7 mmol) in one portion. After 5 min, a few crystals of RuCl3 is added. The reaction is stirred for 3 h and the resulting thick slurry is diluted with water (100 mL) and ethyl acetate (20 mL) and is 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-fdb97cdac1e749c3ae8348e467e30aad
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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