Pyridine → HCID 10751345, compound

HRID 1824673Notes

Reaction equation

HRID 1824673 reaction equation
[C:1]([NH:8][C@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:24]>C(Cl)Cl>[C:4]([O:3][C:1](=[O:2])[NH:8][C@H:9]([C:13]([F:24])=[O:15])[CH:10]([CH3:12])[CH3:11])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 83693Boc-L-Valine

Product 1

HCID 10751345HCID 10751345, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

To an oven-dried, septaed 25 mL round-bottom flask, cooled under an argon atmosphere, and charged with (S)-N-BOC-valine (217.2 mg, 1.00 mmol) was added 2.5 mL CH2Cl2, and pyridine (81 μL, 1.00 mmol). The solution was cooled to −15° C., and to the reaction was added cyanuric fluoride (450 μL, 5.0 mmol). The reaction was stirred at −15° C. for 60 minutes, with the gradual formation of a white precipitate. Without warming, the crude reaction was poured over ice, and immediately extracted twice with CH2Cl2. The combined CH2Cl2 extracts were washed once with ice-cold water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford 201.3 mg of 25g as white needles. FTIR (neat) 1847 cm−1.

Workup

  1. temperaturecooled under an argon atmosphere
  2. temperatureWithout warming
  3. customthe crude reaction
  4. additionwas poured over ice
  5. extractionimmediately extracted twice with CH2Cl2
  6. washThe combined CH2Cl2 extracts were washed once with ice-cold water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-102e6dc772de4f7682d52631ca2e19f6
Source dataset
uspto-grants-2006_05
Patent number
US07045360B2

Reaction notes

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