Potassium Hydroxide → HCID 178516380, compound

HRID 402733Notes

Reaction equation

HRID 402733 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[O:15][C:14]([NH:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[C:13](C(OCC)=O)[C:12]2=[O:27])=[CH:2]1.[OH-].[K+]>C(O)C>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[C:12](=[O:27])[CH:13]=[C:14]([NH:16][CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21]3)[O:15]2)=[CH:2]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178469504HCID 178469504, compound

Product 1

HCID 178516380HCID 178516380, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound (0.10 g, 0.27 mmol) of Example 103 in ethanol (4.0 mL), 50% potassium hydroxide solution (2.0 mL, 0.036 mol) was added at ambient temperature. The mixture was refluxed for 2 h. Cooled to ambient temperature, the solvent was removed under reduced pressure. Water was added to this residue, the mixture was washed with ethyl acetate then 1M hydrochloric acid was added to adjust pH to acidic, and then the solvent was removed under reduced pressure. The residue was purified by preparative HPLC to afford the titled compound as solid (0.0015 g, y. 5%).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customthe solvent was removed under reduced pressure
  3. additionWater was added to this residue
  4. washthe mixture was washed with ethyl acetate
  5. addition1M hydrochloric acid was added
  6. customwas removed under reduced pressure
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-83f15fdfa86c4f58a9dd0bcd2968f584
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

Loading…