Pyridine → HCID 14824271, compound

HRID 1941339Notes

Reaction equation

HRID 1941339 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[C@H:10]([CH2:12][CH3:13])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:25]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([F:25])=[O:16])[C@H:10]([CH2:12][CH3:13])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 2724762tert-Butoxycarbonyl-L-isoleucine

Product 1

HCID 14824271HCID 14824271, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

To a cooled (-15° C.) solution of t-butoxycarbonylisoleucine (0.482 g, 2 mmol) and pyridine (0.16 ml) in methylene chloride (5 ml) is dropped cyanuric fluoride (0.9 ml) and the mixture is stirred at -15° C. for 1 hour. The reaction mixture is diluted with methylene chloride and ice, and filtered on Celite. The filtrate is diluted with ice water and extracted with methylene chloride. The organic layer is dried over magnesium sulfate and concentrated in vacuo to give t-butoxycarbonylisoleucine fluoride.

Workup

  1. filtrationfiltered on Celite
  2. additionThe filtrate is diluted with ice water
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d1c30e1ba19d492b8defc209b745d8ac
Source dataset
uspto-grants-1997_12
Patent number
US05703106

Reaction notes

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