Pyridine → Fmoc-l-leucyl fluoride

HRID 7230

Reaction equation

HRID 7230 reaction equation
[C:1]([NH:18][C@H:19]([C:24]([OH:26])=O)[CH2:20][CH:21]([CH3:23])[CH3:22])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:35]>C(#N)C>[C:1]([NH:18][C@H:19]([C:24]([F:35])=[O:26])[CH2:20][CH:21]([CH3:23])[CH3:22])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 1549133Fmoc-leucine

Product 1

HCID 11121802Fmoc-l-leucyl fluoride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

FMOC-L-Leucine (5 g, 14.14 mmol) (Bachem) was dissolved in acetonitrile (70 mL). Pyridine (1.14 mL, 14.14 mmol) (Aldrich) and cyanuric fluoride (1.91 g, 14.14 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred overnight. Ice cold water (300 mL) was added and the resulting slurry was filtered. The filtrate was poured into a separatory funnel and the layers were separated. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford FMOC-L-leucyl fluoride as a white powder. (Yield 4.57 g, 91%).

Workup

  1. filtrationthe resulting slurry was filtered
  2. additionThe filtrate was poured into a separatory funnel
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9c73895b2c0a498e9c55ac238f8665f2
Source dataset
uspto-grants-2006_08
Patent number
US07084270B2

Linked notes

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