Ethyl Acetate → HCID 58866130, compound

HRID 1354289Notes

Reaction equation

HRID 1354289 reaction equation
[CH2:1]([O:8][NH:9][C:10]([C@H:12]1[C@H:17]2[O:18][C:19]([CH3:22])([CH3:21])[O:20][C@H:16]2[C@@H:15]([O:23]S(C(F)(F)F)(=O)=O)[CH2:14][N:13]1[S:31]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)(=[O:33])=[O:32])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:42]([O-])(=[O:44])[CH3:43].[Cs+].C1OCCOCCOCCOCCOCCOC1.C(OCC)(=O)C>C(#N)C>[CH2:1]([O:8][NH:9][C:10]([C@H:12]1[C@H:17]2[O:18][C:19]([CH3:22])([CH3:21])[O:20][C@@H:16]2[C@H:15]([O:23][C:42](=[O:44])[CH3:43])[CH2:14][N:13]1[S:31]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)(=[O:32])=[O:33])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 2855718-Crown-6HCID 5152919Cesium acetateHCID 87821884HCID 87821884, compound

Product 1

HCID 58866130HCID 58866130, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The above compound (2-1) (670 mg) was dissolved in acetonitrile (30 mL) and cesium acetate (0.5 g) and 18-Crown-6 (1.4 g) were added, and then the mixture was stirred at room temperature for 16 hours, To the reaction solution was added ethyl acetate (100 mL) and, after washing in turn with dilute hydrochloric acid, an aqueous saturated sodium hydrogencarbonate solution and saturated saline, the solution was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3→1:1) to obtain the titled compound (161 mg).

Workup

  1. washafter washing in turn with dilute hydrochloric acid
  2. dry with materialan aqueous saturated sodium hydrogencarbonate solution and saturated saline, the solution was dried over magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3→1:1)

Sources & evidence

ORD record
ord-22191c011ec94be89739422fba8ed1d4
Source dataset
uspto-grants-2007_05
Patent number
US07223779B2

Reaction notes

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