Pyridine → Bis-fmoc-l-lysyl fluoride

HRID 7232

Reaction equation

HRID 7232 reaction equation
[C:1]([N:18]([C:28]([O:30][CH2:31][CH:32]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38]2[C:33]1=[CH:34][CH:35]=[CH:36][CH:37]=2)=[O:29])[C@H:19]([C:25](O)=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])([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:53]>ClCCl>[C:1]([N:18]([C:28]([O:30][CH2:31][CH:32]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38]2[C:33]1=[CH:34][CH:35]=[CH:36][CH:37]=2)=[O:29])[C@H:19]([C:25]([F:53])=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])([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 23385649Bis-fmoc-lysine

Product 1

HCID 131725881Bis-fmoc-l-lysyl fluoride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bis-FMOC-L-Lysine (5 g, 8.46 mmol) (Bachem) was dissolved in dichloromethane (50 mL). Pyridine (0.69 mL, 8.46 mmol) (Aldrich) and cyanuric fluoride (1.14 g, 8.46 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred overnight. Ice cold water (100 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 bis-FMOC-L-lysyl fluoride as a white powder. (Yield 1.14 g, 23%).

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-a20466eb704b4286a24630c1e60bd7a4
Source dataset
uspto-grants-2006_08
Patent number
US07084270B2

Linked notes

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