Potassium Carbonate → Tert-butyl 2-(4-nitro-1H-imidazol-1-YL)ethylcarbamate

HRID 1818932Notes

Reaction equation

HRID 1818932 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:16]([C:19]1[N:20]=[CH:21][NH:22][CH:23]=1)([O-:18])=[O:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][N:22]1[CH:23]=[C:19]([N+:16]([O-:18])=[O:17])[N:20]=[CH:21]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22605302tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamateHCID 178526856HCID 178526856, compound

Product 1

HCID 10422534Tert-butyl 2-(4-nitro-1H-imidazol-1-YL)ethylcarbamateYield 32%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methanesulfonic acid 2-tert-butoxycarbonylamino-ethyl ester (compound 39.1; 2.04 g, 8.53 mmol, prepared according to the procedure of Hey, M. P. et. al J. Med. Chem 37, 1994, 381), 4-nitroimidazole (876 mg, 7.75 mmol), K2CO3 (1.18 g, 8.53 mmol), in DMF is stirred at 110° C. for 2 hours. After cooling to room temperature, the mixture is diluted with EtOAc and washed with water. The aqueous layer was extracted three times with EtOAc and the combined organic phases were dried (Na2SO4) and concentrated. The crude residue was purified by flash column chromatography (SiO2, 45 to 100% EtOAc in hexanes) to yield 634 mg (32%) of [2-(4-nitro-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl ester (compound 39.2) as a solid, ES (+) MS m/e=257 (M+H+).

Workup

  1. custom2.04 g, 8.53 mmol, prepared
  2. washwashed with water
  3. extractionThe aqueous layer was extracted three times with EtOAc
  4. dry with materialthe combined organic phases were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash column chromatography (SiO2, 45 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e95be461a81548c788f655261a51c490
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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