Sodium periodate → HCID 86669713, compound

HRID 1624010Notes

Reaction equation

HRID 1624010 reaction equation
[C:1]([C@H:5]1[CH2:9][O:8][S:7](=[O:10])[N:6]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:19].[Na+]>C(#N)C.O.O.[Ru](Cl)(Cl)Cl>[C:1]([C@H:5]1[CH2:9][O:8][S:7](=[O:19])(=[O:10])[N:6]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 68182344HCID 68182344, compound

Product 1

HCID 86669713HCID 86669713, compoundYield 93.5%

Reagents, catalysts & solvents 3

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a solution of (4S)-4-(tert-butyl)-3-(phenylmethyl)-1,2,3-oxathiazolidine-2-oxide (6.26 g, 24.71 mmol) in acetonitrile (30 mL) and water (30 mL) at 0° C. was added ruthenium chloride hydrate (5.13 mg, 0.025 mmol), followed by sodium periodate (7.93 g, 37.1 mmol). The reaction mixture was slowly warmed to room temperature and stirred for 3 h, diluted with water, extracted with ethyl acetate. The combined organics were washed with water, dried over anhydrous Na2SO4, filtered then concentrated to give the title compound (6.22 g) as an off-white solid. LCMS m/z=270.2 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 1.00 (s, 9H), 3.25-3.30 (m, 1H), 4.31-4.40 (m, 2H), 4.47 and 4.55 (dd, J=15.2 Hz, 2H), 7.30-7.48 (m, 5H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationthen concentrated

Sources & evidence

ORD record
ord-61d395f249ef49c5ad3ceccda182d0a7
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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