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2-Nitroimidazole → 5-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane

HRID 514617
Notes
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Reaction equation

HRID 514617 reaction equation
Br[CH2:2][C:3]1([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]1.[N+:20]([C:23]1[NH:24][CH:25]=[CH:26][N:27]=1)([O-:22])=[O:21].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O.O>[O:12]([CH2:11][C:3]1([CH2:2][N:24]2[CH:25]=[CH:26][N:27]=[C:23]2[N+:20]([O-:22])=[O:21])[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]1)[Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 107012-NitroimidazoleHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 903004745-Bromomethyl-5-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-1,3-dioxane

Product 1

HCID 903005825-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxaneYield 57.4%

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

578 mg (1.64 mmol equivalents) of 5-bromomethyl-5-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-1,3-dioxane was dissolved in 10 mL of dimethylformamide, 186 mg (1.64 mmol equivalents) of 2-nitroimidazole and 680 mg (4.92 mmol equivalents) of potassium carbonate were added thereto, and the mixture was heated to 100° C. for 18 hours. After completion of the reaction, the reaction liquid was cooled to room temperature (25° C.), a saturated aqueous solution of ammonium chloride and water were added thereto, and the mixture was extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water and brine, then dried with anhydrous magnesium sulfate and subsequently concentrated under vacuum, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=3/1) to give 363 mg (0.942 mmol equivalents) of 5-(t-butyldimethylsiloxymethyl)-2,2-dimethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. temperaturewas cooled to room temperature (25° C.)
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with water and brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationsubsequently concentrated under vacuum
  8. customthe obtained crude product
  9. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=3/1)

Sources & evidence

ORD record
ord-39ac64494d3d4088a937819bd9bda618
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09107964B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes