Pyridine → HCID 86760074, compound

HRID 1824674Notes

Reaction equation

HRID 1824674 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C(F)=NC(F)=NC=1[F:19].N1C=CC=CC=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([C:10]([F:19])=[O:11])[C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid

Product 1

HCID 86760074HCID 86760074, compoundYield 65.2%

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 24h (170.3 mg, 0.74 mmol) was added 2.0 mL freshly distilled CH2Cl2 under argon. The reaction was cooled to −15 C and to the flask was added cyanuric fluoride (335 μL, 3.7 mmol). The reaction was stirred at −15 C for 15 minutes then anhydrous pyridine (60 μL, 0.74 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 112.6 mg of a mixture of 24h and 25h as an off-white solid.

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-9bf7019f9e3b4738a1cd72e6d8865ec2
Source dataset
uspto-grants-2006_05
Patent number
US07045360B2

Reaction notes

Loading…