Chloromethyl Methyl Ether → HCID 19932989, compound

HRID 326466Notes

Reaction equation

HRID 326466 reaction equation
C(OC([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[N:10]=[CH:9]1)=O)(C)(C)C.[CH3:23][O:24][CH2:25]Cl.C(=O)([O-])O.[Na+]>C(#N)C>[C:19]([O:18][C:16]([NH:15][CH2:14][CH2:13][C:11]1[N:10]([CH2:23][O:24][CH3:25])[CH:9]=[N:8][CH:12]=1)=[O:17])([CH3:20])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 516892Sodium BicarbonateHCID 819122tert-butyl 4-{2-[(tert-butoxycarbonyl)amino]ethyl}-1H-imidazole-1-carboxylate

Product 1

HCID 19932989HCID 19932989, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-t-Butoxycarbonyl-4-{2-(t-butoxycarbonyl-amino)ethyl}imidazole (78.1 g) is dissolved in acetonitrile (500 ml), and thereto is added methoxymethyl chloride (22.2 g), and the mixture is stirred at room temperature overnight. The reaction solution is poured into 10% aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract is washed, dried, and the solvent is distilled off to give 4-{2-(t-butoxycarbonyl-amino)ethyl]-3-methoxymethylimidazole (54.4 g) as oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed
  3. customdried
  4. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-bea66919b5d84a29b23af46ad0ecc4d6
Source dataset
uspto-grants-1993_12
Patent number
US05268377

Reaction notes

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