Isopropanol → 5-(Methyl-propylcarbamoyl)-isophthalic acid monoisopropyl ester

HRID 1436624Notes

Reaction equation

HRID 1436624 reaction equation
[CH:1]([O:4][C:5](=[O:24])[C:6]1[CH:7]=[C:8]([CH:14]=[C:15]([C:17](=[O:23])[N:18]([CH3:22])[CH2:19][CH2:20][CH3:21])[CH:16]=1)[C:9]([O:11]CC)=[O:10])([CH3:3])[CH3:2].C(O)(C)C.[OH-].[Li+]>[OH-].[Na+].O>[CH:1]([O:4][C:5](=[O:24])[C:6]1[CH:16]=[C:15]([C:17](=[O:23])[N:18]([CH3:22])[CH2:19][CH2:20][CH3:21])[CH:14]=[C:8]([C:9]([OH:11])=[O:10])[CH:7]=1)([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 3939Lithium HydroxideHCID 688145695-(Methyl-propylcarbamoyl)-isophthalic acid 1-ethyl ester 3-isopropyl ester

Product 1

HCID 688144435-(Methyl-propylcarbamoyl)-isophthalic acid monoisopropyl esterYield 64.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

Stir a solution of 5-(methyl-propylcarbamoyl)-isophthalic acid 1-ethyl ester 3-isopropyl ester (149 mg, 0.4 mmol) in 0.2 N NaOH in 1:10 water:isopropanol (2.2 mL) overnight. Add 1 N lithium hydroxide (0.44 mL) and stir for 1 h at room temperature. Dilute with water and extract with dichloromethane. Acidify the aqueous with 5 N HCl, extract the aqueous with dichloromethane, dry (magnesium sulfate) and concentrate to give the title compound (79 mg, 56%).

Workup

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

Sources & evidence

ORD record
ord-dd3d13a818304680b38da7cef4f84ea0
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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