Dichloromethane → HCID 58508441, compound

HRID 454625Notes

Reaction equation

HRID 454625 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].C(Cl)Cl.Cl.[OH:12][C:13]1[CH:36]=[CH:35][C:34]([O:37][CH:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)=[CH:33][C:14]=1[C:15]([NH:17][C:18]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:19]=1[C:20]([OH:22])=[O:21])=[O:16]>N1C=CC=CC=1>[C:1]([N:41]1[CH2:40][CH2:39][CH:38]([O:37][C:34]2[CH:35]=[CH:36][C:13]([OH:12])=[C:14]([CH:33]=2)[C:15]([NH:17][C:18]2[CH:26]=[C:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:24]=[CH:23][C:19]=2[C:20]([OH:22])=[O:21])=[O:16])[CH2:43][CH2:42]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic Anhydride2×HCID 66991248HCID 66991248, compound

Product 1

HCID 58508441HCID 58508441, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Under ice-cooling, pyridine (0.30 mL) and acetic anhydride (6.7 μL) were sequentially added to a methylene chloride (1 mL) suspension of 2-(2-hydroxy-5-(piperidin-4-yloxy)benzamido)-4-phenylbenzoic acid hydrochloride (0.030 g), followed by stirring at room temperature for 1 hour. Pyridine (0.20 mL) and acetic anhydride (5.4 μL) were sequentially added to the reaction mixture, followed by stirring at room temperature for 1 hour and 30 minutes. The solvent was evaporated under reduced pressure, and methanol (0.5 mL) and a 2 mol/L aqueous solution of sodium hydroxide (0.19 mL) were added to the residue, followed by stirring at room temperature for 1 hour. To the reaction mixture, 1 mol/L hydrochloric acid (5 mL) and ethyl acetate were added. The organic layer was separated, washed with 1 mol/L hydrochloric acid, water, and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Dioxane (0.5 mL), methanol (0.5 mL), and a 2 mol/L aqueous solution of sodium hydroxide (0.32 mL) were added to the obtained residue, followed by stirring at 70° C. for 30 minutes. After cooling the reaction mixture to room temperature, the solvent was evaporated under reduced pressure, and water was added to the obtained residue. After adjusting the pH to 3 with 6 mol/L hydrochloric acid, the solid substance was collected by filtration to obtain 0.022 g of 2-(5-(1-acetylpiperidin-4-yloxy)-2-hydroxybenzamido)-4-phenylbenzoic acid as a white solid.

Workup

  1. temperatureUnder ice-cooling
  2. stirringby stirring at room temperature for 1 hour and 30 minutes
  3. customThe solvent was evaporated under reduced pressure, and methanol (0.5 mL)
  4. additiona 2 mol/L aqueous solution of sodium hydroxide (0.19 mL) were added to the residue
  5. stirringby stirring at room temperature for 1 hour
  6. additionTo the reaction mixture, 1 mol/L hydrochloric acid (5 mL) and ethyl acetate were added
  7. customThe organic layer was separated
  8. washwashed with 1 mol/L hydrochloric acid, water
  9. dry with materiala saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. additionDioxane (0.5 mL), methanol (0.5 mL), and a 2 mol/L aqueous solution of sodium hydroxide (0.32 mL) were added to the obtained residue
  12. stirringby stirring at 70° C. for 30 minutes
  13. temperatureAfter cooling the reaction mixture to room temperature
  14. customthe solvent was evaporated under reduced pressure, and water
  15. additionwas added to the obtained residue
  16. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-66f01708d74545ac8c2c8529fbc046e9
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

Loading…