Chloromethyl Methyl Ether → HCID 19932989, compound

HRID 21881Notes

Reaction equation

HRID 21881 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+].[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 10340Sodium CarbonateHCID 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-butoxycarbonylamino)ethyl]imidazole (78.1 g) is dissolved in acetonitrile (500 ml), and thereto is added methoxymethyl chloride (22.2 g). The mixture is stirred at room temperature overnight, and poured into aqueous 10% sodium carbonate solution, and extracted with ethyl acetate. The extract is washed, dried and evaporated to give 5-[2-(t-butoxycarbonylamino)ethyl]1-methoxymethylimidazole (54.4 g) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-c3008c843851484088435efbc7278fab
Source dataset
uspto-grants-1995_06
Patent number
US05424316

Reaction notes

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