Sodium periodate → HCID 86669708, compound

HRID 1623995Notes

Reaction equation

HRID 1623995 reaction equation
[O:1]=[S:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:5]([CH:14]([CH3:16])[CH3:15])[CH2:4][O:3]1.I([O-])(=O)(=O)=[O:18].[Na+]>C(#N)C.O.[Ru](Cl)(Cl)Cl>[O:1]=[S:2]1(=[O:18])[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@@H:5]([CH:14]([CH3:16])[CH3:15])[CH2:4][O:3]1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 67060930HCID 67060930, compound

Product 1

HCID 86669708HCID 86669708, compoundYield 29.7%

Reagents, catalysts & solvents 3

HCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To an ice-cooled solution of (4S)-2-oxo-3-benzyl-4-isopropyl-1,2,3-oxathiazolidine (6.00 g, 25.07 mmol) in acetonitrile (45 mL) and water (45.0 mL) was added ruthenium chloride (5.20 mg, 0.025 mmol) followed by sodium periodate (8.04 g, 37.6 mmol). The mixture was stirred for 1 h as ice bath melted and the reaction was gradually warmed to room temperature. The mixture was extracted with ether (3×50 mL). The combined organic extracts were washed with brine (100 mL), dried (MgSO4), filtered, then concentrated. The resulting oil was purified by silica gel flash column chromatography to give the title compound (1.9 g) as a colorless oil. LCMS m/z=256.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 0.86 (d, J=7.1 Hz, 3H), 0.90 (d, J=7.1 Hz, 3H), 1.83-1.95 (m, 1H), 3.41-3.45 (m, 1H), 4.23-4.28 (m, 2H), 4.39-4.44 (m, 2H), 7.35-7.43 (m, 5H).

Workup

  1. extractionThe mixture was extracted with ether (3×50 mL)
  2. washThe combined organic extracts were washed with brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting oil was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-32dc44dad9854d799efb66b27b1b5856
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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