Water → HCID 57805529, compound

HRID 2104130Notes

Reaction equation

HRID 2104130 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[O-:27][Mn](=O)(=O)=O.[K+].CCOC(C)=O.[OH2:39]>CC(C)=O>[O:39]=[C:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:18]([C:15]1[CH:14]=[CH:13][C:12]([C:8]2([NH:7][C:6](=[O:26])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:9][CH2:10][CH2:11]2)=[CH:17][CH:16]=1)=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 516875Potassium PermanganateHCID 57805483HCID 57805483, compound

Product 1

HCID 57805529HCID 57805529, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of tert-butyl{1-[4-(phenylethynyl)phenyl]cyclobutyl}carbamate (7-3, 6.65 g, 19.14 mmol) in anhydrous acetone (38.3 ml) was added KMnO4 (12.10 g, 77 mmol). The reaction mixture was heated to 35° C. for 2 hours. The reaction mixture was cooled to room temperature and EtOAc and water were added to the mixture. The suspension was filtered through a glass frit and the filtrate was extracted into EtOAc, washing with water and brine. The organic layer was dried over Na2SO4, filtered and reduced in vacuo to give 7-4 as a brown oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe suspension was filtered through a glass frit
  3. extractionthe filtrate was extracted into EtOAc
  4. washwashing with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-0150af40716f4b628091124ce45d43f4
Source dataset
uspto-grants-2009_08
Patent number
US07576209B2

Reaction notes

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