Sodium hydride → Methyl 3-(dipropylcarbamoyl)-5-(2-oxopyrrolidin-1-yl)benzoate

HRID 852649Notes

Reaction equation

HRID 852649 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:18]=[C:17]([NH:19][C:20](=[O:25])[CH2:21][CH2:22][CH2:23]Cl)[CH:16]=[C:6]([C:7]([N:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[H-].[Na+]>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:18]=[C:17]([N:19]2[CH2:23][CH2:22][CH2:21][C:20]2=[O:25])[CH:16]=[C:6]([C:7]([N:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 693578475-(4-Chloro-butanoylamino)-N,N-dipropyl-isophthalamic acid methyl ester

Product 1

HCID 69357886Methyl 3-(dipropylcarbamoyl)-5-(2-oxopyrrolidin-1-yl)benzoateYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(4-chloro-butanoylamino)-N,N-dipropyl-isophthalamic acid methyl ester (D89) (1.7 g, 4.4 mmol, 1 equiv) THF (20 ml) was treated portionwise with NaH (60% dispersion in mineral oil, 180 mg, 4.5 mmol, 1.1 equiv) and the resulting mixture was stirred for 1 h and then was diluted with AcOEt (100 ml). The resulting solution was washed with 2N aqueous HCl solution (50 ml), dried over MgSO4 and concentrated in vacuo to give 5-(2-oxo-pyrrolidin-1-yl)-N,N-dipropyl-isophthalamic acid methyl ester (B80) (1.38 g, 91%) as a colourless oil.

Workup

  1. washThe resulting solution was washed with 2N aqueous HCl solution (50 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5e17eef14b54657b87fc603f7106cc3
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

Loading…