Methyl iodide → HCID 68716239, compound

HRID 29334Notes

Reaction equation

HRID 29334 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([CH:11]=[CH2:12])=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([NH:31][C@H:32]([C:36]([O:38][CH3:39])=[O:37])[CH:33]([CH3:35])[CH3:34])(=[O:30])=[O:29])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)=[O:14].[C:40](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH3:40][N:31]([S:28]([C:25]1[CH:26]=[CH:27][C:22]([C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:13]([C:3]3[O:4][C:5]4[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]=[CH2:12])[C:6]=4[C:2]=3[CH3:1])=[O:14])=[CH:21][CH:20]=2)=[CH:23][CH:24]=1)(=[O:30])=[O:29])[C@H:32]([C:36]([O:38][CH3:39])=[O:37])[CH:33]([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68714271methyl N-[(4'-{[(3-methyl-4-vinyl-1-benzofuran-2-yl)carbonyl]amino}-1,1'-biphenyl-4-yl)sulfonyl]-L-valinate

Product 1

HCID 68716239HCID 68716239, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.077 g (0.14 mmol) of the product of Example 96, Step 2, methyl N-[(4′-{[(3-methyl-4-vinyl-1-benzofuran-2-yl)carbonyl]amino}-1,1′-biphenyl-4-yl)sulfonyl]-L-valinate, in 1 mL of DMF, 0.05 g of potassium carbonate were added, followed by 0.018 mL of iodomethane. The reaction was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was extracted with dichloromethane. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated to provide 0.1 g of methyl N-methyl-N-[(4′-{[(3-methyl-4-vinyl-1-benzofuran-2-yl)carbonyl]amino}-1,1′-biphenyl-4-yl)sulfonyl]-L-valinate. Yield 63.4%. MS: 561 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionthe residue was extracted with dichloromethane
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0d702e1997574a25ba474b083f5b89e0
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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