Lithium Hydroxide → 3-Ethylcarbamoyl-5-(methyl-propylcarbamoyl)-benzoic acid

HRID 1436620Notes

Reaction equation

HRID 1436620 reaction equation
C([O:3][C:4](=[O:23])[C:5]1[CH:10]=[C:9]([C:11](=[O:17])[N:12]([CH3:16])[CH2:13][CH2:14][CH3:15])[CH:8]=[C:7]([C:18](=[O:22])[NH:19][CH2:20][CH3:21])[CH:6]=1)C.[OH-].[Li+].C1COCC1>O>[CH2:20]([NH:19][C:18]([C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([C:11](=[O:17])[N:12]([CH3:16])[CH2:13][CH2:14][CH3:15])[CH:8]=1)[C:4]([OH:23])=[O:3])=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 688150393-Ethylcarbamoyl-5-(methyl-propylcarbamoyl)-benzoic acid ethyl ester

Product 1

HCID 688173383-Ethylcarbamoyl-5-(methyl-propylcarbamoyl)-benzoic acidYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Stir a solution of 3-ethylcarbamoyl-5-(methyl-propylcarbamoyl)-benzoic acid ethyl ester (157 mg, 0.5 mmol), 1 N aqueous lithium hydroxide (2.45 mL, 2.45 mmol) and THF (2.45 mL) at room temperature overnight. Dilute the reaction with water and extract with dichloromethane. Acidify the aqueous with 5 N HCl , extract the aqueous with dichloromethane and dry (magnesium sulfate) and concentrate to give the title compound (106 mg, 74%).

Workup

  1. additionDilute
  2. extractionextract with dichloromethane
  3. extractionextract the aqueous with dichloromethane
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-1f80e735611a41dd8ab948e34044b5cd
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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