4-Toluenesulfonyl chloride → HCID 89472108, compound

HRID 514629Notes

Reaction equation

HRID 514629 reaction equation
[CH3:1][C:2]1([CH3:24])[O:7][CH2:6][C:5]([CH2:22][OH:23])([CH2:8][N:9]2[CH:13]=[C:12]([CH2:14][O:15][CH2:16][O:17][CH3:18])[N:11]=[C:10]2[N+:19]([O-:21])=[O:20])[CH2:4][O:3]1.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.[Cl-].[NH4+]>C(N(CC)CC)C>[CH3:1][C:2]1([CH3:24])[O:3][CH2:4][C:5]([CH2:8][N:9]2[CH:13]=[C:12]([CH2:14][O:15][CH2:16][O:17][CH3:18])[N:11]=[C:10]2[N+:19]([O-:21])=[O:20])([CH2:22][O:23][S:31]([C:28]2[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=2)(=[O:33])=[O:32])[CH2:6][O:7]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 25517Ammonium ChlorideHCID 903004272,2-dimethyl-5-hydroxymethyl-5-[(4-methoxymethoxymethyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane

Product 1

HCID 89472108HCID 89472108, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

23 mg (0.11 mmol equivalents) of 2,2-dimethyl-5-hydroxymethyl-5-[(4-methoxymethoxymethyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane was dissolved in 1.0 mL of triethylamine, 1 mg (0.01 mmol equivalents) of N,N-dimethylaminopyridine and 23 mg (0.12 mmol equivalents) of p-toluenesulfonyl chloride were added thereto, and the mixture was stirred at room temperature (25° C.) for 16 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted three times with ethyl acetate. The combined ethyl acetate layers were dried with anhydrous magnesium sulfate, and then concentrated under vacuum. The obtained crude product was purified by flash silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=1/3) to give 16 mg (0.03 mmol equivalents) of 2,2-dimethyl-5-[(4-methoxymethoxymethyl-2-nitro-1H-imidazol-1-yl)methyl]-5-(p-toluenesulfonyloxymethyl)-1,3-dioxane.

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. dry with materialThe combined ethyl acetate layers were dried with anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe obtained crude product
  6. customwas purified by flash silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=1/3)

Sources & evidence

ORD record
ord-f8138b32121e4b8c983687ccab0f7baa
Source dataset
uspto-grants-2015_08
Patent number
US09107964B2

Reaction notes

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