Potassium Carbonate → (S)-N-[5-(1,2-dihydroxy-ethyl)-pyrazin-yl]-2,2-dimethyl-propionamide

HRID 719959Notes

Reaction equation

HRID 719959 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].[CH3:7][C:8]([CH3:21])([CH3:20])[C:9]([NH:11][C:12]1[CH:17]=[N:16][C:15]([CH:18]=[CH2:19])=[CH:14][N:13]=1)=[O:10].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[OH2:31].C(O)(C)(C)C>[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+].[Os](=O)(=O)(=O)=O.CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1.C1(C)C=CC=CC=1>[OH:31][C@@H:18]([C:15]1[N:16]=[CH:17][C:12]([NH:11][C:9](=[O:10])[C:8]([CH3:21])([CH3:20])[CH3:7])=[N:13][CH:14]=1)[CH2:19][OH:2]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 656671Sodium PyrosulfiteHCID 21897227N-(5-Ethenyl-2-pyrazinyl)-2,2-dimethyl-propanamideHCID 714019492-Methylpropan-2-ol--water (1/1)2×

Product 1

HCID 51349106(S)-N-[5-(1,2-dihydroxy-ethyl)-pyrazin-yl]-2,2-dimethyl-propionamideYield 100%

Reagents, catalysts & solvents 4

HCID 1140TolueneCatalystHCID 30318Osmium TetroxideCatalystHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazineCatalystHCID 178511488HCID 178511488, compoundCatalyst

Conditions

Temperature
25 °C

Procedure

A mixture of potassium ferricyanide (148.74 g, 450 mmol), potassium carbonate (62.25 g, 450 mmol), and (DHQ)2PHAL (2.6 g, 3.34 mmol) was treated with a solution of water/tert-butyl alcohol (2 L, 1:1), and the reaction mixture was stirred at 25° C. for 15 min. The reaction mixture was cooled to 5° C., treated with a 0.2M solution of osmium tetroxide in toluene (7.5 mL, 1.5 mmol), and then treated with 2,2-dimethyl-N-(5-vinyl-pyrazin-2-yl)-propionamide (30.8 g, 150 mmol) which was partially dissolved in water/tert-butyl alcohol (150 mL, 1:1). The mixture was stirred at 4–5° C. for 18 h using a Neslab Endocal cooling system to control the temperature. While stirring at 4–5° C., the mixture was then slowly treated with sodium metabisulfite (35 g, 184 mmol) which resulted in effervescence. The cooling bath was removed, and the stirring continued for 15 min. The layers were separated, and the aqueous layer was extracted with ethyl acetate (600 mL). Each organic layer was washed with a saturated aqueous sodium chloride solution (500 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford N-[5-(1(S),2-dihydroxy-ethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide (46 g, 100%) as a red oil which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to 5° C.
  2. stirringThe mixture was stirred at 4–5° C. for 18 h
  3. temperaturecooling system
  4. stirringWhile stirring at 4–5° C.
  5. customresulted in effervescence
  6. customThe cooling bath was removed
  7. waitthe stirring continued for 15 min
  8. customThe layers were separated
  9. extractionthe aqueous layer was extracted with ethyl acetate (600 mL)
  10. washEach organic layer was washed with a saturated aqueous sodium chloride solution (500 mL)
  11. dry with materialThe combined organic layers were dried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51e0dd1f31b54783b024bc234ba4bbc0
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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