Ethyl Acetate → HCID 22940401, compound

HRID 842641Notes

Reaction equation

HRID 842641 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C@H:9]2[CH2:11][C@H:10]2[NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)=[O:14])[CH:6]=[CH:7][CH:8]=1)#[CH:2].C(OCC)(=[O:25])C.C([O-])([O-])=O.[K+].[K+]>OS(O)(=O)=O.O.C(O)(=O)C.[Hg](OC(C)=O)OC(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([C@H:9]2[CH2:11][C@H:10]2[NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)=[O:14])[CH:6]=[CH:7][CH:8]=1)(=[O:25])[CH3:2]

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 22940404HCID 22940404, compound

Product 1

HCID 22940401HCID 22940401, compound

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 1118Sulfuric AcidCatalystHCID 16683746DiacetyloxymercuryCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of (+,−)-N-(cis-2-(3-Ethynylphenyl)-cyclopropyl)-N′-(5-chloropyrid-2-yl)-urea of Example 22(130 mg, 0.42 mmole), H2SO4 (10 drops), H2O (10 drops) and Hg(OAc)2 (100 mg) in acetic acid (4 mL) was stirred at room temperature for 30 min. The reaction mixture was then poured into an ethyl acetate and saturated K2CO3 solution. The organic layer was dried (MgSO4) and the solvent was evaporated to give a residue which was purified on silica gel using 1:1 acetone: and hexanes as the eluent providing 43 mg of the title compound.

Workup

  1. dry with materialThe organic layer was dried (MgSO4)
  2. customthe solvent was evaporated
  3. customto give a residue which
  4. customwas purified on silica gel using 1:1 acetone

Sources & evidence

ORD record
ord-be84e8343a3f407eaaf6aa4956653ab5
Source dataset
uspto-grants-2002_04
Patent number
US06376492B1

Reaction notes

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