Pyridine → HCID 14824293, compound

HRID 1824676Notes

Reaction equation

HRID 1824676 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 11010409(2S)-2-(((tert-butoxy)carbonyl)amino)-2-phenylacetic acid

Product 1

HCID 14824293HCID 14824293, compoundYield 91%

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 24k (125.8 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 warming, 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 115.3 mg of a mixture of 24k and 25k 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. temperatureWithout warming
  6. customthe crude reaction
  7. additionwas poured over ice
  8. extractionimmediately extracted twice with CH2Cl2
  9. washThe combined CH2Cl2 extracts were washed once with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77d53cb28c124d18be3af484389fb0e0
Source dataset
uspto-grants-2006_05
Patent number
US07045360B2

Reaction notes

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