Methyl iodide → HCID 18713364, compound

HRID 279056Notes

Reaction equation

HRID 279056 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]2=[O:24])=[CH:10][CH:9]=1)=[O:7].[H-].[Na+].I[CH3:28]>CN(C=O)C>[CH3:28][N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]2=[O:24])=[CH:10][CH:9]=1)=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57081651HCID 57081651, compound

Product 1

HCID 18713364HCID 18713364, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

The title compound of Example 47 (0.14 g, 0.43 mM) in DMF (1.4 ml) was stirred under nitrogen and cooled to 5° C. Sodium hydride (0.019 g of a 60% dispersion in mineral oil, 0.47 mM) was added and the mixture stirred for 15 minutes. Iodomethane (30 μl) was added, the mixture stirred for 10 minutes at 5° C. and at ambient temperature for 2 hours. The mixture was evaporated and the residue partitioned between EtOAc and water. The organic layer was washed with water dried (MgSO4) and evaporated. The residue was purified by column chromatography in dichloromethane, eluting with a gradient increasing in polarity from 2% to 10% MeOH/dichloromethane to give the title product as an oil (0.13 g). MS: 342 (MH+); NMR: 1.83 (3H, s); 3.28 (nH+H2O); 3.42 (2H, t); 3.80 (1H, m); 3.92 (3H, s); 4.9 (1H, t); 4.75 (1H, m); 6.16 (1H, m); 6.64 (1H, m); 7.23 (1H, m); 7.67 (2H, d); 7.80 (2H, d); 8.22 (1H, t).

Workup

  1. stirringthe mixture stirred for 10 minutes at 5° C. and at ambient temperature for 2 hours
  2. customThe mixture was evaporated
  3. customthe residue partitioned between EtOAc and water
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography in dichloromethane
  8. washeluting with
  9. temperaturea gradient increasing in polarity from 2% to 10% MeOH/dichloromethane

Sources & evidence

ORD record
ord-8775ea59073f47ff9c1e335583843707
Source dataset
uspto-grants-2002_03
Patent number
US06362191B1

Reaction notes

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