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

HRID 514623Notes

Reaction equation

HRID 514623 reaction equation
Br[CH2:2][C:3]1([CH2:11][O:12][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]1.[N+:30]([C:33]1[NH:34][CH:35]=[CH:36][N:37]=1)([O-:32])=[O:31].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[O:12]([CH2:11][C:3]1([CH2:2][N:34]2[CH:35]=[CH:36][N:37]=[C:33]2[N+:30]([O-:32])=[O:31])[CH2:4][O:5][C:6]([CH3:10])([CH3:9])[O:7][CH2:8]1)[Si:13]([C:26]([CH3:27])([CH3:29])[CH3:28])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 107012-NitroimidazoleHCID 11430Potassium CarbonateHCID 903003725-Bromomethyl-5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-1,3-dioxane

Product 1

HCID 903003695-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxaneYield 19.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1.70 g (3.56 mmol equivalents) of 5-bromomethyl-5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-1,3-dioxane was dissolved in 36 mL of dimethylformamide, 402 mg (3.56 mmol equivalents) of 2-nitroimidazole and 1.48 g (10.7 mmol equivalents) of potassium carbonate were added thereto, and the mixture was heated in an oil bath to 80° C. and then stirred for 18 hours. After completion of the reaction, water was added dropwise, and the mixture was extracted with ethyl acetate three times. The combined ethyl acetate layers were washed with water and brine, then dried with anhydrous magnesium sulfate, and subsequently concentrated under vacuum. The obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=3/1) to give 362 mg (0.71 mmol equivalents) of 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane.

Workup

  1. additionwas added dropwise
  2. extractionthe mixture was extracted with ethyl acetate three times
  3. washThe combined ethyl acetate layers were washed with water and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationsubsequently concentrated under vacuum
  6. customThe obtained crude product
  7. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=3/1)

Sources & evidence

ORD record
ord-2d7209fed2424164bd29dc262fd73ea6
Source dataset
uspto-grants-2015_08
Patent number
US09107964B2

Reaction notes

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