Cyanuric chloride → 1-[(S)-N-(tert-Butoxycarbonyl)-4-fluoro-beta-methyl-L-phenylalanyl]-2-cyanopyrrolidine

HRID 970209Notes

Reaction equation

HRID 970209 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:19]([N:21]1[CH2:28][CH2:27][CH2:26][C@H:22]1[C:23]([NH2:25])=O)=[O:20])[C@@H:10]([CH3:18])[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:19]([N:21]1[CH2:28][CH2:27][CH2:26][CH:22]1[C:23]#[N:25])=[O:20])[CH:10]([CH3:18])[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 69417947(betaS)-N-(tert-Butoxycarbonyl)-4-fluoro-beta-methyl-L-phenylalanyl-L-prolinamide

Product 1

HCID 694214941-[(S)-N-(tert-Butoxycarbonyl)-4-fluoro-beta-methyl-L-phenylalanyl]-2-cyanopyrrolidine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the product from Step A (91.7 mg, 0.233 mmol) in anhydrous DMF (1 mL) was added cyanuric chloride (86 mg, 0.466 mmol). After stirring at room temperature for 16 h, the reaction was diluted with ethyl acetate. The organic phase was washed sequentially with water, saturated aqueous sodium bicarbonate solution and brine, dried (magnesium sulfate), and concentrated under reduced pressure. Purification by preparative thin layer chromatography (silica, ethyl acetate eluant) afforded the title compound.

Workup

  1. washThe organic phase was washed sequentially with water, saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customPurification by preparative thin layer chromatography (silica, ethyl acetate eluant)

Sources & evidence

ORD record
ord-5d09004fcb66463897bd6147d6d70e5b
Source dataset
uspto-grants-2007_12
Patent number
US07309714B2

Reaction notes

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