Pyridine → HCID 14824294, compound

HRID 1824675Notes

Reaction equation

HRID 1824675 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C(F)=NC(F)=NC=1[F:21].N1C=CC=CC=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([C:10]([F:21])=[O:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 2755953(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid

Product 1

HCID 14824294HCID 14824294, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an oven-dried, septaed 25 mL round-bottom flask, cooled under an argon atmosphere, and charged with 24j (124.9 mg, 0.50 mmol) was added 1.25 mL freshly distilled CH2Cl2 under argon. The reaction was cooled to −15 C and to the flask was added cyanuric fluoride (225 μL, 2.5 mmol). The reaction was stirred at −15 C for 15 minutes then anhydrous pyridine (40 μL, 0.5 mmol) was added. Stirring was maintained at −15 C for 60 minutes. Without warning, the crude reaction was poured over ice, and immediately extracted twice with CH2Cl2. The combined CH2Cl2 extracts were washed once with water, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford 114.8 mg of a mixture of 24j and 25j as an off-white solid. FTIR (film) 1849.3 cm−1.

Workup

  1. temperaturecooled under an argon atmosphere
  2. temperatureThe reaction was cooled to −15 C and to the flask
  3. stirringStirring
  4. temperaturewas maintained at −15 C for 60 minutes
  5. customWithout warning, the crude reaction
  6. additionwas poured over ice
  7. extractionimmediately extracted twice with CH2Cl2
  8. washThe combined CH2Cl2 extracts were washed once with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3dcd448113a04f029559311e392e83b6
Source dataset
uspto-grants-2006_05
Patent number
US07045360B2

Reaction notes

Loading…