water acetonitrile CCl4 → HCID 86718384, compound

HRID 1518772Notes

Reaction equation

HRID 1518772 reaction equation
[O:1]1C=CC=[C:2]1[C@@H:6]([N:12]([CH3:20])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:7]([CH3:11])[CH2:8][O:9][CH3:10].[OH2:21].C(Cl)(Cl)(Cl)Cl.CC#N>C(#N)C>[C:15]([O:14][C:13]([N:12]([CH3:20])[C@@H:6]([C@H:7]([CH3:11])[CH2:8][O:9][CH3:10])[C:2]([OH:1])=[O:21])=[O:19])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 22592919water acetonitrile CCl4HCID 86718385HCID 86718385, compound

Product 1

HCID 86718384HCID 86718384, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of NalO4 (0.83 g, 3.87 mmol, 6.0 equiv) in water/CCl4/acetonitrile (3/2/3, 17.9 mL) was added RuCl3 (45.0 mg, 0.22 mmol, 0.34 equiv) at room temperature. After stirring for 15 minutes, a solution of compound 2.1c (0.183 g, 0.65 mmol) in acetonitrile (2.0 mL) was added. After stirring for another 15 minutes, the reaction was quenched with water. The aqueous layer was extracted with ethyl acetate. Combined organic layer was washed with brine, dried with Na2SO4, filtered and concentrated in vacuo to afford compound 3.1b (0.17 g).

Workup

  1. stirringAfter stirring for another 15 minutes
  2. customthe reaction was quenched with water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washCombined organic layer was washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-07929d07c2964c01b6f5994941ffd8e2
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

Loading…