Imidazole → HCID 54483345, compound

HRID 266353Notes

Reaction equation

HRID 266353 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH2:19][CH:20]([CH2:35]OS(C2C(C)=CC=CC=2)(=O)=O)[C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:26][CH:25]=2)=[O:22])(=[O:17])=[O:16])=[CH:11][CH:10]=1>CN(C=O)C>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([S:15]([NH:18][CH2:19][CH:20]([CH2:35][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[C:21]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:29]=2)=[O:22])(=[O:17])=[O:16])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 86751113HCID 86751113, compound

Product 1

HCID 54483345HCID 54483345, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of imidazole (6.9 mg) in DMF (0.5 ml) was added to a 60% NaH (4.0 mg) suspension in anhydrous DMF (0.5 ml) prepared at 0° C., under argon. After stirring for 20 minutes, a DMF solution of (RS)-2-(4-chlorobenzenesulfonylaminomethyl)-N-(4-ethoxycarbonylphenyl)-3-toluenesulfonyloxypropanamide (12 mg) was added. The whole was stirred at 0° C. to room temperature overnight. The reaction mixture was poured into a saturated saline solution and extracted with ethyl acetate. The combined ethyl acetate layers were washed with a saturated saline solution and dried over Na2SO4. The solvent was evaporated, and the residue was purified by column chromatography (6% water-containing silica gel, chloroform/methanol=5/1) to obtain the desired (RS)-2-(4-chlorobenzenesulfonylaminomethyl)-N-(4-ethoxycarbonylphenyl)-3-(1H-imidazol-1-yl)propanamide (7 mg).

Workup

  1. customprepared at 0° C., under argon
  2. stirringThe whole was stirred at 0° C. to room temperature overnight
  3. additionThe reaction mixture was poured into a saturated saline solution
  4. extractionextracted with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with a saturated saline solution
  6. dry with materialdried over Na2SO4
  7. customThe solvent was evaporated
  8. customthe residue was purified by column chromatography (6% water-containing silica gel, chloroform/methanol=5/1)

Sources & evidence

ORD record
ord-fd801b31e9f944aaa269229a3bd2864f
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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