Pyridine → Fmoc-d-methionyl fluoride

HRID 7235Notes

Reaction equation

HRID 7235 reaction equation
[C:1]([NH:18][C@@H:19]([C:24]([OH:26])=O)[CH2:20][CH2:21][S:22][CH3:23])([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]>ClCCl>[C:1]([NH:18][C@@H:19]([C:24]([F:35])=[O:26])[CH2:20][CH2:21][S:22][CH3:23])([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 6992521(2R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(methylsulfanyl)butanoic acid

Product 1

HCID 23544816Fmoc-d-methionyl fluoride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

FMOC-D-Methionine (5.00 g, 13.46 mmol) (Bachem) was dissolved in dichloromethane (70 mL). Pyridine (1.09 mL, 13.46 mmol) (Aldrich) and cyanuric fluoride (1.82 g, 13.46 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred for 4 hours. 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 FMOC-D-methionyl fluoride as a white powder. (Yield 3.7 g., 74%).

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-ff701405dbdb4c8d96cc24948af218ae
Source dataset
uspto-grants-2006_08
Patent number
US07084270B2

Reaction notes

Loading…