Water → HCID 57805529, compound

HRID 2064452Notes

Reaction equation

HRID 2064452 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-:27][Mn](=O)(=O)=O.[K+].CCOC(C)=O.[OH2:39]>CC(C)=O>[O:39]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[CH2:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=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-4ba13fa24c5343039cea7e4e4070fe80
Source dataset
uspto-grants-2012_10
Patent number
US08288407B2

Reaction notes

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