Hydrochloric Acid → HCID 17974763, compound

HRID 900743Notes

Reaction equation

HRID 900743 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][N:4]1[C:9]([SH:10])=[CH:8][C:7](=[O:11])[N:6]([CH3:12])[C:5]1=[O:13].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24](=O)[C:25]([O:27][CH2:28][CH3:29])=[O:26].Cl>CN(C)C=O.ClCCl.[Ti](Cl)(Cl)(Cl)Cl.O>[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][N:4]1[C:9]2[S:10][CH:23]=[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:8]=2[C:7](=[O:11])[N:6]([CH3:12])[C:5]1=[O:13]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 66144Ethyl bromopyruvateHCID 17974706HCID 17974706, compound

Product 1

HCID 17974763HCID 17974763, compound

Reagents, catalysts & solvents 4

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To the product of step b) (6.3 g) in dry dimethylformamide (100 ml) was added potassium carbonate (1.9 g) and stirred for 10 min. Ethyl bromopyruvate (4 ml) was added and was stirred under nitrogen at room temperature for 2 h. The reaction was poured into water (1 L) and acidified (2M HCl) and extracted with ethyl acetate. The combined organics were washed with brine (100 ml). Drying and evaporation afforded an oil. The oil was dissolved in dichloromethane (100 ml) and cooled in ice whilst stirring. Titanium tetrachloride (6 ml) was added and stirring continued under nitrogen for 2 hours. The reaction was poured into water (1 L) and extracted with dichloromethane (×2). The combined organics were dried and concentrated in vacuo. The residue was purified by chromatography (SiO2/ethyl acetate-dichloromethane 0-8%) to afford the subtitle compound as an orange oil, 6.2 g

Workup

  1. stirringwas stirred under nitrogen at room temperature for 2 h
  2. extractionextracted with ethyl acetate
  3. washThe combined organics were washed with brine (100 ml)
  4. customDrying
  5. customevaporation
  6. customafforded an oil
  7. temperaturecooled in ice
  8. stirringwhilst stirring
  9. stirringstirring
  10. waitcontinued under nitrogen for 2 hours
  11. extractionextracted with dichloromethane (×2)
  12. customThe combined organics were dried
  13. concentrationconcentrated in vacuo
  14. customThe residue was purified by chromatography (SiO2/ethyl acetate-dichloromethane 0-8%)

Sources & evidence

ORD record
ord-677a8dd362884c36829ab27c659e4c07
Source dataset
uspto-grants-2008_04
Patent number
US07361660B2

Reaction notes

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