Pyridine → Fmoc-phenylalanine fluoride

HRID 7229

Reaction equation

HRID 7229 reaction equation
[C:1]([NH:18][C@H:19]([C:27]([OH:29])=O)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([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:38]>ClCCl>[C:1]([NH:18][C@H:19]([C:27]([F:38])=[O:29])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([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 978331Fmoc-phenylalanine

Product 1

HCID 11811187Fmoc-phenylalanine fluoride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

FMOC-L-Phenylalanine (17 g, 44 mmol) (Bachem) was dissolved in dichloromethane (100 mL). Pyridine (3.55 mL, 44 mmol) (Aldrich) and cyanuric fluoride (6 g, 44 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred for 3.5 hours. 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-phenylalanyl fluoride as a white powder. (Yield 13.6 g, 80%).

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-eb09cec98f6f4f36902d1ca683505650
Source dataset
uspto-grants-2006_08
Patent number
US07084270B2

Linked notes

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