Pyridine → HCID 57004208, compound

HRID 393479Notes

Reaction equation

HRID 393479 reaction equation
C[O:2][C:3](=[O:37])[C@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:32](=[O:33])[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([C:34]#[N:35])[CH:30]=3)[C:25]2=[O:36])=[CH:20][CH:19]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][O:15][CH3:16])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[I-].[Li+].N1C=CC=CC=1>O>[C:34]([C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][CH:28]=1)[C:25](=[O:36])[N:24]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][C@@H:4]([C:3]([OH:37])=[O:2])[NH:5][C:6]([C:8]3([CH2:13][CH2:14][O:15][CH3:16])[CH2:12][CH2:11][CH2:10][CH2:9]3)=[O:7])=[CH:23][CH:22]=1)[C:32]2=[O:33])#[N:35]

Participants

5

Reactant 3

HCID 1049PyridineHCID 66321Lithium iodideHCID 54318505HCID 54318505, compound

Product 1

HCID 57004208HCID 57004208, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-(5-cyano-1,3-dioxo-2H-isoindol-2-yl)-N-[[1-(2-methoxyethyl)cyclopentyl]carbonyl]-L-phenylalanine methyl ester (0.3 mmol, 151 mg) and lithium iodide (3.0 mmol, 397 mg) was added pyridine (6 mL) at room temperature. The solution was refluxed for 15 h at which time TLC analysis of the mixutre indicated the absence of starting material. Then, it was cooled to room temperature and diluted with water (15 mL) and the bulk of the pyridine was removed by concentration under reduced pressure. The residue was extracted with ether (2×15 mL) to remove any neutral impurities. The aqueous layer was acidified with 1N HCl and the precipitated white solid was collected by filtration and washed with 20 mL of water and 20 mL of hexane. After air-drying, the crude product was purified by reverse phase HPLC to afford 50 mg (34%) of a white solid, mp 143-146° C. HR MS (C27H27N3O6): Obs mass, 490.1990. Calcd mass, 490.1978 (M+H).

Workup

  1. temperatureThe solution was refluxed for 15 h at which time TLC analysis of the mixutre
  2. customthe bulk of the pyridine was removed by concentration under reduced pressure
  3. extractionThe residue was extracted with ether (2×15 mL)
  4. customto remove any neutral impurities
  5. filtrationthe precipitated white solid was collected by filtration
  6. washwashed with 20 mL of water and 20 mL of hexane
  7. customAfter air-drying
  8. customthe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-2dd299c310b34ab9b38662fe669672d5
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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