Potassium Iodide → Benzyl (4R)-4-t-butoxycarbonylamino-5-(5-cyano-2-iodophenoxy)pentanoate

HRID 49923Notes

Reaction equation

HRID 49923 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:22]Cl)[CH2:10][CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[I:33])[C:28]#[N:29].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:22][O:24][C:25]1[CH:26]=[C:27]([C:28]#[N:29])[CH:30]=[CH:31][C:32]=1[I:33])[CH2:10][CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 109446813-Hydroxy-4-iodobenzonitrileHCID 86588383benzyl (4R)-4-t-butoxycarbonylamino-5-chloropentanoate

Product 1

HCID 86588382Benzyl (4R)-4-t-butoxycarbonylamino-5-(5-cyano-2-iodophenoxy)pentanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.29 g (24.3 mmol) of benzyl (4R)-4-t-butoxycarbonylamino-5-chloropentanoate, 6.9 g (28.0 mmol) of 3-hydroxy-4-iodobenzonitrile, 6.9 g (50 mmol) of potassium carbonate and 4.15 g (25 mmol) of potassium iodide were stirred together in 80 ml of DMF at 70° C. for 3 days. The solvent was evaporated, and the crude product obtained by an ordinary method with ethyl acetate as the extracting solvent was purified by the silica gel chromatography (ethyl acetate/hexane) to obtain the title compound.

Workup

  1. customThe solvent was evaporated
  2. customthe crude product obtained by an ordinary method with ethyl acetate as the extracting solvent
  3. customwas purified by the silica gel chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c807bc373e22470a8a175de1074e5d81
Source dataset
uspto-grants-2004_03
Patent number
US06710056B2

Reaction notes

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