Pyridine → HCID 59072564, compound

HRID 393473Notes

Reaction equation

HRID 393473 reaction equation
C[O:2][C:3](=[O:36])[C@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]2[CH:32]=[C:31]([C:33]#[N:34])[CH:30]=[CH:29][C:28]=2[Cl:35])=[O:26])=[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>[Cl:35][C:28]1[CH:29]=[CH:30][C:31]([C:33]#[N:34])=[CH:32][C:27]=1[C:25]([NH:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][C@@H:4]([C:3]([OH:36])=[O:2])[NH:5][C:6]([C:8]2([CH2:13][CH2:14][O:15][CH3:16])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:7])=[CH:19][CH:20]=1)=[O:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 66321Lithium iodideHCID 541472274-[(2-chloro-5-cyanophenylcarbonyl)amino]-N-[[1-(2-methoxy-ethyl)cyclopentyl]carbonyl]-L-phenylalanine methyl ester

Product 1

HCID 59072564HCID 59072564, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-[(2-chloro-5-cyanophenylcarbonyl)amino]-N-[[1-(2-methoxy-ethyl)cyclopentyl]carbonyl]-L-phenylalanine methyl ester (0.1 mmol, 51 mg) and lithium iodide (1.0 mmol, 133 mg) was added pyridine (2 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, the mixture was cooled to room temperature and diluted with water (15 mL) and the bulk of the pyridine was removed under reduced pressure. Then it 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 crystallized from acetonitrile to afford 20 mg (40%) of a white solid: mp 169-172° C. HR MS (C26H26ClN3O5): Obs mass, 498.1802. Calcd mass, 498.1795, 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 under reduced pressure
  3. extractionThen it 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 crystallized from acetonitrile

Sources & evidence

ORD record
ord-74883518ee4d463f8c6794c26e9c90b0
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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