Ethyl bromoacetate → 2-{3-[3-(1-Triphenylmethyl-imidazol-4-yl)-propyl]-5-methyl-5-naphthalen-1-yl-2,4-dioxo-imidazolidin-1-yl}-acetic acid ethyl ester

HRID 1934813Notes

Reaction equation

HRID 1934813 reaction equation
[C:1]1([C:7]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][N:16]3[C:20](=[O:21])[C:19]([CH3:32])([C:22]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[CH:25]=[CH:24][CH:23]=4)[NH:18][C:17]3=[O:33])[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49].[H-].[Na+]>CN(C)C=O>[CH2:51]([O:50][C:48](=[O:49])[CH2:47][N:18]1[C:19]([CH3:32])([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)[C:20](=[O:21])[N:16]([CH2:15][CH2:14][CH2:13][C:11]2[N:10]=[CH:9][N:8]([C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH:12]=2)[C:17]1=[O:33])[CH3:52]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 224668503-[3-(1-Triphenylmethyl-imidazol-4-yl)-propyl]-5-methyl-5-naphthalen-1-yl-imidazolidin-2,4-dione

Product 1

HCID 572281992-{3-[3-(1-Triphenylmethyl-imidazol-4-yl)-propyl]-5-methyl-5-naphthalen-1-yl-2,4-dioxo-imidazolidin-1-yl}-acetic acid ethyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.082 g(0.14 mmol) of 3-[3-(1-triphenylmethyl-imidazol-4-yl)-propyl]-5-methyl-5-naphthalen-1-yl-imidazolidin-2,4-dione prepared in Example 1-1) and 0.023 ml(0.21 mmol) of ethyl bromoacetate were dissolved in 5 ml of dimethylformamide. 0.017 g(0.21 mmol) of sodium hydride [NaH] was added thereto and the resulting solution was stirred for one hour. Dimethylformamide was removed under reduced pressure and the residue was dissolved in ethyl acetate and then washed with saturated sodium chloride solution. Removal of ethyl acetate under reduced pressure provided 0.092 g(Yield: 99%) of title compound.

Workup

  1. customDimethylformamide was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. customRemoval of ethyl acetate under reduced pressure

Sources & evidence

ORD record
ord-2bd0fcd875e24c319a7a18386932374c
Source dataset
uspto-grants-2002_05
Patent number
US06384061B1

Reaction notes

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