Water → HCID 71205442, compound

HRID 2280864Notes

Reaction equation

HRID 2280864 reaction equation
[CH:1]([N:4]1[C:8]([CH:9]2[CH2:12][C:11](=C)[CH2:10]2)=[CH:7][C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:5]1)([CH3:3])[CH3:2].[OH2:19]>CC#N.[O-]S([O-])(=S)=O.[Na+].[Na+].C(Cl)Cl>[CH:1]([N:4]1[C:8]([CH:9]2[CH2:12][C:11](=[O:19])[CH2:10]2)=[CH:7][C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 962Water3×HCID 89370568HCID 89370568, compound

Product 1

HCID 71205442HCID 71205442, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

Compound 8c (6.45 g, 26.0 mmol) was dissolved in a mixture of MeCN (77 mL) and water (13 mL) and cooled in an ice-bath. To this solution RuCl3×H2O (0.19 g, 0.86 mmol) was added, followed by portion-wise addition of NaIO4 (19.35 g, 90.9 mmol). An exotherm was observed during this addition. The obtained thick slurry was stirred at rt for 45 min. The reaction mixture was diluted with Na2S2O3 aq. sol. (10%, 260 mL), water (50 mL) and DCM (100 mL). The phases were separated and the aq. phase was extracted with DCM (2×70 mL). The combined organic phases were washed with Na2S2O3 aq. sol. (10%, 50 mL), water (100 mL), brine (100 mL) and dried over anh. Na2SO4. The crude product (6.5 g) was purified on silica, eluting with hexanes/MTBE to give pure product as an oil that solidified upon storage at −20° C. Yield: 5.8 g (78% over two steps). 1H-NMR (DMSO-d6), δ (ppm): 6.78 (s, 1H), 4.57 (h, J=8.0 Hz, 1H), 4.26 (q, J=8.0 Hz, 2H), 3.85-3.75 (m, 1H), 3.58-3.45 (m, 2H), 3.35-3.25 (m, 2H), 1.39 (d, J=8.0 Hz, 6H), 1.28 (t, J=8.0 Hz, 3H).

Workup

  1. temperaturecooled in an ice-bath
  2. additionAn exotherm was observed during this addition
  3. customThe phases were separated
  4. extractionthe aq. phase was extracted with DCM (2×70 mL)
  5. washThe combined organic phases were washed with Na2S2O3 aq. sol. (10%, 50 mL), water (100 mL), brine (100 mL)
  6. dry with materialdried over anh. Na2SO4
  7. customThe crude product (6.5 g) was purified on silica
  8. washeluting with hexanes/MTBE
  9. customto give pure product as an oil that
  10. customsolidified upon storage at −20° C

Sources & evidence

ORD record
ord-c024604c5fca41f18ee2928ee29b34f1
Source dataset
uspto-grants-2015_09
Patent number
US09139539B2

Reaction notes

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