Lithium Hydroxide → HCID 68815235, compound

HRID 732501Notes

Reaction equation

HRID 732501 reaction equation
C([O:3][C:4](=[O:26])[C:5]1[CH:17]=[C:16]([C:18]([N:20]2[CH2:24][CH2:23][CH2:22][CH:21]2[CH3:25])=[O:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)C.[OH-].[Li+].C1COCC1>O>[CH3:14][N:10]([CH2:11][CH2:12][CH3:13])[C:8](=[O:9])[C:7]1[CH:6]=[C:5]([CH:17]=[C:16]([C:18]([N:20]2[CH2:24][CH2:23][CH2:22][CH:21]2[CH3:25])=[O:19])[CH:15]=1)[C:4]([OH:26])=[O:3]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68817196HCID 68817196, compound

Product 1

HCID 68815235HCID 68815235, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Stir a solution of N-methyl-5-(2-methylpyrrolidine-1-carbonyl)-N-propyl-isophthalamic acid ethyl ester (218 mg, 0.6 mmol), 1 N lithium hydroxide (2.4 mL, 2.4 mmol) and THF (2.4 mL) at room temperature overnight. Add 50 mL water and extract with dichloromethane (3×10 mL). Acidify the aqueous with 1 N HCl (3 mL) and extract with dichloromethane (3×10 mL). Dry (sodium sulfate) and concentrate to give the title compound (216 mg, 100%).

Workup

  1. extractionextract with dichloromethane (3×10 mL)
  2. extractionextract with dichloromethane (3×10 mL)
  3. dry with materialDry (sodium sulfate)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-7d57b37145ef47a8aaf32540589f3944
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

Loading…