4-Toluenesulfonyl chloride → HCID 90300383, compound

HRID 514639Notes

Reaction equation

HRID 514639 reaction equation
[CH3:1][C:2]1([CH3:20])[O:7][CH2:6][C:5]([CH2:18][OH:19])([CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[N+:15]([O-:17])=[O:16])[CH2:4][O:3]1.N12CCN(CC1)CC2.[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1.[Cl-].[NH4+]>ClCCl>[CH3:1][C:2]1([CH3:20])[O:7][CH2:6][C:5]([CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[N+:15]([O-:17])=[O:16])([CH2:18][O:19][S:35]([C:32]2[CH:33]=[CH:34][C:29]([CH3:39])=[CH:30][CH:31]=2)(=[O:37])=[O:36])[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 9237DabcoHCID 25517Ammonium ChlorideHCID 903005492,2-dimethyl-5-hydroxymethyl-5-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-1,3-dioxane

Product 1

HCID 90300383HCID 90300383, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

25 mg (0.086 mmol equivalents) of 2,2-dimethyl-5-hydroxymethyl-5-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-1,3-dioxane was dissolved in 1 mL of dichloromethane, 19 mg (0.172 mmol equivalents) of 1,4-diazabicyclo[2,2,2]octane and 19 mg (0.10 mmol equivalents) of p-toluenesulfonyl chloride were added thereto, and the mixture was stirred at room temperature (25° C.) for 4 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 silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=1/3) to give 18 mg (0.041 mmol equivalents) of 2,2-dimethyl-5-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-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 silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=1/3)

Sources & evidence

ORD record
ord-846b42a29b214e368187c37889fa48ff
Source dataset
uspto-grants-2015_08
Patent number
US09107964B2

Reaction notes

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