Hydrochloric Acid → HCID 58508941, compound

HRID 454688Notes

Reaction equation

HRID 454688 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][CH2:40][OH:41])[CH2:34][CH2:33]2)=[CH:25][C:5]=1[C:6]([NH:8][C:9]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=[CH:15][C:10]=1[C:11]([O:13]C)=[O:12])=[O:7].O.Cl>CO.O1CCOCC1.C(OCC)(=O)C>[OH:3][C:4]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][CH2:40][OH:41])[CH2:34][CH2:33]2)=[CH:25][C:5]=1[C:6]([NH:8][C:9]1[CH:18]=[C:17]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:16]=[CH:15][C:10]=1[C:11]([OH:13])=[O:12])=[O:7]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 58508551HCID 58508551, compound

Product 1

HCID 58508941HCID 58508941, compoundYield 60.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A 2.0 mol/L aqueous solution of sodium hydroxide (0.031 mL) was added to a solution mixture of the obtained methyl 2-(2-hydroxy-5-(2-(4-(3-hydroxypropyl)piperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate (0.011 g) in methanol (1.0 mL) and dioxane (1.0 mL), followed by stirring at 50° C. for 1 hour. A 2.0 mol/L aqueous solution of sodium hydroxide (0.031 mL) was added to the reaction mixture, followed by stirring at 50° C. for 1 hour. The reaction mixture was cooled to room temperature, and then water was added thereto. After adjusting the pH to 6.5 with 1.0 mol/L hydrochloric acid, ethyl acetate was added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined. The resulting mixture was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration to obtain 6.5 mg of 2-(2-hydroxy-5-(2-(4-(3-hydroxypropyl)piperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoic acid as a light yellow solid.

Workup

  1. stirringby stirring at 50° C. for 1 hour
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additionwas added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe resulting mixture was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. additionDiisopropyl ether was added to the obtained residue
  10. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-502af8c7bace46b4b01962e74fc8f6a7
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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