Methyl iodide → HCID 86757279, compound

HRID 651613Notes

Reaction equation

HRID 651613 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH2:12][N:13]3[CH2:17][CH2:16][C@H:15]([NH:18][S:19]([C:22]4[CH:31]=[CH:30][C:29]5[C:24](=[CH:25][C:26]([O:32][CH3:33])=[CH:27][CH:28]=5)[CH:23]=4)(=[O:21])=[O:20])[C:14]3=[O:34])=[CH:7][CH:8]=2)[N:3]=1.[CH3:35]I.[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH2:12][N:13]3[CH2:17][CH2:16][C@H:15]([N:18]([CH3:35])[S:19]([C:22]4[CH:31]=[CH:30][C:29]5[C:24](=[CH:25][C:26]([O:32][CH3:33])=[CH:27][CH:28]=5)[CH:23]=4)(=[O:20])=[O:21])[C:14]3=[O:34])=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53831072HCID 53831072, compound

Product 1

HCID 86757279HCID 86757279, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

7-Methoxynaphthalene-2-sulfonic acid [1-(2-chloro-quinolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-amide (0.4 g, 0.81 mmol), prepared as in EXAMPLE 15, Part F, is dissolved in DMF (20 mL) and cooled to 0° C. To the solution is added methyl iodide (0.28 g, 2.01 mmol) and sodium hydride (34 mg, 0.85 mmol, 60% mineral oil dispersion). The ice water bath is removed and the mixture is stirred at room temperature for 3 hours. The resulting solution is poured into a separatory funnel and diluted with EtOAc (100 mL). The organic layer is washed with 1N HCl, H2O and saturated NaCl. The organic phase is then dried over MgSO4, filtered and concentrated. The crude residue is purified by column chromatography eluting with 10% EtOAc/CH2Cl2 to give the title compound (0.36 g, 0.71 mmol) as a solid.

Workup

  1. customThe ice water bath is removed
  2. additionThe resulting solution is poured into a separatory funnel
  3. additiondiluted with EtOAc (100 mL)
  4. washThe organic layer is washed with 1N HCl, H2O and saturated NaCl
  5. dry with materialThe organic phase is then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue is purified by column chromatography
  9. washeluting with 10% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-8f26e2d376234b4e8647b7f444728406
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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