Hydrochloric Acid → 2-(5-(2-(Azetidin-1-yl)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoic acid hydrochloride

HRID 454697Notes

Reaction equation

HRID 454697 reaction equation
[OH-].[Na+].CC(O)C.[N:7]1([CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([OH:39])=[C:18]([CH:38]=2)[C:19]([NH:21][C:22]2[CH:31]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:29]=[CH:28][C:23]=2[C:24]([O:26]C)=[O:25])=[O:20])[CH2:10][CH2:9][CH2:8]1.[ClH:40]>O>[ClH:40].[N:7]1([CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([OH:39])=[C:18]([CH:38]=2)[C:19]([NH:21][C:22]2[CH:31]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:29]=[CH:28][C:23]=2[C:24]([OH:26])=[O:25])=[O:20])[CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 58508869Methyl 2-(5-(2-(azetidin-1-yl)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoate

Product 1

HCID 669903602-(5-(2-(Azetidin-1-yl)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A 2.0 mol/L aqueous solution of sodium hydroxide (0.11 mL) was added to a 2-propanol (1.0 mL) suspension of the obtained methyl 2-(5-(2-(azetidin-1-yl)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoate (0.032 g), followed by stirring at 50° C. for 1 hour. The reaction mixture was cooled to room temperature, and water was added thereto. After adjusting the pH to 6.0 with 1.0 mol/L hydrochloric acid, the solid substance was collected by filtration. Ethyl acetate (1.5 mL) and a 4.0 mol/L hydrogen chloride-dioxane solution (0.10 mL) were added to the obtained solid substance, followed by stirring at room temperature for 1 hour and 30 minutes. The solid substance was collected from the reaction mixture by filtration to obtain 0.021 g of 2-(5-(2-(azetidin-1-yl)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoic acid hydrochloride as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe solid substance was collected by filtration
  3. additionEthyl acetate (1.5 mL) and a 4.0 mol/L hydrogen chloride-dioxane solution (0.10 mL) were added to the obtained solid substance
  4. stirringby stirring at room temperature for 1 hour and 30 minutes
  5. filtrationThe solid substance was collected from the reaction mixture by filtration

Sources & evidence

ORD record
ord-6cbdc4712b9042ab94746ed82dcd5bcf
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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