Lithium iodide → N-({4'-[(1-benzofuran-2-ylcarbonyl)amino]-1,1'-biphenyl-4-yl}sulfonyl)-N-methyl-D-valine

HRID 29317Notes

Reaction equation

HRID 29317 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([N:28]([CH3:37])[C@@H:29]([C:33]([O:35]C)=[O:34])[CH:30]([CH3:32])[CH3:31])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)=[O:11].[I-].[Li+]>C(OCC)(=O)C.Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([N:28]([CH3:37])[C@@H:29]([C:33]([OH:35])=[O:34])[CH:30]([CH3:32])[CH3:31])(=[O:26])=[O:27])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)=[O:11]

Participants

5

Reactant 2

HCID 66321Lithium iodideHCID 68710769methyl N-({4'-[(1-benzofuran-2-ylcarbonyl)amino]-1,1'-biphenyl-4-yl}sulfonyl)-N-methyl-D-valinate

Product 1

HCID 59788415N-({4'-[(1-benzofuran-2-ylcarbonyl)amino]-1,1'-biphenyl-4-yl}sulfonyl)-N-methyl-D-valineYield 78.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To 0.13 g of methyl N-({4′-[(1-benzofuran-2-ylcarbonyl)amino]-1,1′-biphenyl-4-yl}sulfonyl)-N-methyl-D-valinate in 12 mL ethyl acetate was added 0.67 g of lithium iodide and the mixture was refluxed overnight. The reaction was diluted with ethyl acetate and 1N HCl. The organic layer was washed with water, sodium thiosulfate solution, water and brine, dried over Na2SO4, filtered, and concentrated to provide 0.099 g of N-({4′-[(1-benzofuran-2-ylcarbonyl)amino]-1,1′-biphenyl-4-yl}sulfonyl)-N-methyl-D-valine. Yield 77.9%. m.p. 239-241° C.; MS 505.1(M−H)−.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. washThe organic layer was washed with water, sodium thiosulfate solution, water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-511c2bd31fb342a4823b00f1fc323a79
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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