Diethyl Ether → HCID 178525512, compound

HRID 1500504Notes

Reaction equation

HRID 1500504 reaction equation
COC1C=C(OC)C=CC=1C[N:12]([C:24]1[CH:29]=[C:28]([O:30]C)[C:27]([C:32](=[O:47])[NH:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:36]=2)=[CH:26][N:25]=1)[C:13](=[O:23])[CH2:14][CH2:15][C:16]([O:18]C(C)(C)C)=[O:17].CCOCC>FC(F)(F)C(O)=O>[OH:30][C:28]1[C:27]([C:32](=[O:47])[NH:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:36]=2)=[CH:26][N:25]=[C:24]([NH:12][C:13](=[O:23])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:29]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 117777994HCID 117777994, compound

Product 1

HCID 178525512HCID 178525512, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
40 °C

Procedure

A solution of the mixture (345 mg) containing tert-butyl 4-[(2,4-dimethoxyphenyl)methyl-{4-methoxy-5-[(3-phenylphenyl)methylcarbamoyl]-2-pyridyl}amino]-4-oxobutanoate in trifluoroacetic acid (4 mL) was left standing at room temperature for 17 hours. Ether (60 mL) was added to the reaction solution. The resulting suspension was filtered, and the product collected by filtration was washed with ether and dried under reduced pressure. To the obtained residue, a solution of boron tribromide in dichloromethane (1 M, 6 mL) was added at room temperature, and the mixture was stirred at 40° C. for 6 hours. The reaction mixture was cooled to room temperature, and water was then added thereto. The resulting suspension was filtered, and the product collected by filtration was washed with water and ether. The obtained residue was suspended in ethanol, and the suspension was shaken for 15 minutes in an ultrasonic bath and then filtered. The product collected by filtration was dried under reduced pressure to obtain the title compound (56.7 mg).

Workup

  1. waitwas left
  2. filtrationThe resulting suspension was filtered
  3. filtrationthe product collected by filtration
  4. washwas washed with ether
  5. customdried under reduced pressure
  6. additionTo the obtained residue, a solution of boron tribromide in dichloromethane (1 M, 6 mL) was added at room temperature
  7. temperatureThe reaction mixture was cooled to room temperature
  8. additionwater was then added
  9. filtrationThe resulting suspension was filtered
  10. filtrationthe product collected by filtration
  11. washwas washed with water and ether
  12. stirringthe suspension was shaken for 15 minutes in an ultrasonic bath
  13. filtrationfiltered
  14. filtrationThe product collected by filtration
  15. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-64b79036e413439194a3734280d49223
Source dataset
uspto-grants-2015_12
Patent number
US09206168B2

Reaction notes

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