water acetonitrile CCl4 → HCID 86718367, compound

HRID 1518760Notes

Reaction equation

HRID 1518760 reaction equation
[C:1]([O:5][C:6](=[O:23])[N:7]([C@H:9]([C:18]1[O:19]C=CC=1)[C@H:10]([CH3:17])[CH2:11][CH2:12][C:13]([OH:16])([CH3:15])[CH3:14])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[OH2:24].C(Cl)(Cl)(Cl)Cl.CC#N>CC#N.[Ru](Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:7]([CH3:8])[C@@H:9]([C@H:10]([CH3:17])[CH2:11][CH2:12][C:13]([OH:16])([CH3:14])[CH3:15])[C:18]([OH:19])=[O:24])=[O:23])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 22592919water acetonitrile CCl4HCID 86718368HCID 86718368, compound

Product 1

HCID 86718367HCID 86718367, compound

Reagents, catalysts & solvents 2

HCID 61850Ruthenium trichlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Ruthenium(III) chloride (0.031 g, 0.15 mmol) was added to a well-stirred mixture of NalO4 (0.567 g, 2.65 mmol) in water/CCl4/CH3CN (4.5/3/4.5 mL). After 15 minutes of stirring, at 0° C., 2.12e (0.144 g, 0.442 mmol) in MeCN (0.3 mL) was added. After stirring at room temperature for 30 minutes, another 1 equivalent of NalO4 was added and the resulting mixture was stirred for another 20 minutes. The reaction was quenched with water and extracted with ethyl acetate three times. The combined ethyl acetate layer was washed with 20% NaHSO3 aq. solution and brine, dried over MgSO4 and concentrated to give 2.12f (134 mg) which was used in the next step with out purification. MS m/z (M+23) 326.2.

Workup

  1. stirringAfter stirring at room temperature for 30 minutes
  2. additionanother 1 equivalent of NalO4 was added
  3. stirringthe resulting mixture was stirred for another 20 minutes
  4. customThe reaction was quenched with water
  5. extractionextracted with ethyl acetate three times
  6. washThe combined ethyl acetate layer was washed with 20% NaHSO3 aq. solution and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7188c0af424542a9a47797a792eeab81
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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