Sodium hydride → HCID 140412946, compound

HRID 1859166Notes

Reaction equation

HRID 1859166 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][NH:9][C:8](=[O:12])[C:7]1=[O:13].[H-].[Na+].Br[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33](=[NH:45])[NH:34][C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:36])=[CH:29][CH:28]=1>CN(C)C=O>[CH2:38]([O:37][C:35]([NH:34][C:33]([C:30]1[CH:29]=[CH:28][C:27]([O:26][CH2:25][CH2:24][CH2:23][N:9]2[CH2:10][CH2:11][N:6]([CH2:5][C:4]3[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:3]=3[O:2][CH3:1])[C:7](=[O:13])[C:8]2=[O:12])=[CH:32][CH:31]=1)=[NH:45])=[O:36])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 127069801-[(2,4-Dimethoxyphenyl)methyl]piperazine-2,3-dioneHCID 140397781HCID 140397781, compound

Product 1

HCID 140412946HCID 140412946, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

In 10 ml of N,N-dimethylformamide was dissolved 1.00 g of 1-(2,4-dimethoxybenzyl)-2,3-dioxopiperazine, and 0.17 g of sodium hydride (60%, oil) was added to the solution, followed by stirring at 50° C. for 30 minutes. Then, the reaction mixture was cooled to room temperature, after which 1.48 g of 1-bromo-3-(4-benzyloxycarbonylamidinophenoxy)propane was added thereto and the resulting mixture was stirred overnight at the same temperature. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=20:1) to obtain 1.76 g of 4-[3-(4-benzyloxycarbonylamidinophenoxy)propyl]-1-(2,4-dimethoxybenzyl)-2,3-dioxopiperazine as colorless crystals.

Workup

  1. additionwas added to the solution
  2. temperatureThen, the reaction mixture was cooled to room temperature
  3. stirringthe resulting mixture was stirred overnight at the same temperature
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-257cfae75dae4b2a8ff2b7c3343e89e0
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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