Ethyl bromopyruvate → HCID 59251305, compound

HRID 1466437Notes

Reaction equation

HRID 1466437 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[NH:19])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]([CH3:18])[CH3:17])=[CH:4][CH:3]=1.Br[CH2:21][C:22](=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)(O)[O-].[Na+]>C(O)(C)C>[CH2:26]([O:25][C:23]([C:22]1[N:19]=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]([CH3:17])[CH3:18])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH:21]=1)=[O:24])[CH3:27]

Participants

5

Reactant 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 178438936HCID 178438936, compound

Product 1

HCID 59251305HCID 59251305, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a 250 mL round bottom flask attached with condenser was added N-(4-Bromo-phenyl)-2-isopropyl-benzamidine (1.94 g, 6.11 mmol), ethyl bromopyruvate (1.54 mL, 12.2 mmol), sodium bicarbonate (1.02 g, 12.2 mmol), and iso-propanol (45 mL). The reaction slurry was allowed to stir at 80° C. for approximately 2 hrs. The reaction solution was decanted into a clean round bottom flask and concentrated in vacuo. The resulting residue was dissolved in acetic acid (25 mL), and the solution was allowed to stir at reflux for approximately 2 hrs. The solution was concentrated in vacuo, and the product residue was taken into EtOAc (200 mL) and washed with aq NaCl (200 mL×2) and aq NaHCO3 (100 mL). The organic phase was partitioned, dried over Na2SO4, filtered, concentrated, and chromatographed through a 40 g SiO2 column using a mobile gradient of 100% Fix to 70% EtOAc to afford 1.90 g (75% yield) of title compound. MS (ES): 414.0 [M+H]+.

Workup

  1. customTo a 250 mL round bottom flask attached with condenser
  2. customThe reaction solution was decanted into a clean round bottom flask
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resulting residue was dissolved in acetic acid (25 mL)
  5. stirringto stir
  6. temperatureat reflux for approximately 2 hrs
  7. concentrationThe solution was concentrated in vacuo
  8. washwashed with aq NaCl (200 mL×2) and aq NaHCO3 (100 mL)
  9. customThe organic phase was partitioned
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customchromatographed through a 40 g SiO2 column

Sources & evidence

ORD record
ord-81e00690868e403289a93aa97e75932e
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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