Ethyl bromopyruvate → HCID 10812182, compound

HRID 1166388Notes

Reaction equation

HRID 1166388 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[NH:20])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Br[CH2:27][C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:12][CH:11]=3)[CH2:27][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])([OH:34])[N:20]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 1785047964-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide

Product 1

HCID 10812182HCID 10812182, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (Example 1, step 1) (1.00 g, 3.34 mmol), sodium bicarbonate (544 mg, 6.47 mmol), and ethyl bromopyruvate (1.40 g, 7.19 mmol) in 50 ml of isopropanol was stirred at reflux for 7 hours. After cooling, the mixture was evaporated. The residue was partitioned between dichloromethane and water, and the aqueous layer further extracted with dichloromethane. The combined organic extracts were dried over sodium sulfate, filtered, and evaporated. Chromatography of the residue over silica gel using mixtures of ethyl acetate and toluene as eluents gave the title compound as a pale yellow solid: mp (DSC) 162° C. Anal. Calc'd. for C19H19ClN2O5S (MW 422.89): C, 53.96; H, 4.53; N, 6.62. Found: C, 53.99, H, 4.49; N, 6.42.

Workup

  1. temperatureat reflux for 7 hours
  2. temperatureAfter cooling
  3. customthe mixture was evaporated
  4. customThe residue was partitioned between dichloromethane and water
  5. extractionthe aqueous layer further extracted with dichloromethane
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-463b51d5ed3349d196e3dd889706ce67
Source dataset
uspto-grants-2003_09
Patent number
US06613789B2

Reaction notes

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