Water → HCID 23614997, compound

HRID 1768457Notes

Reaction equation

HRID 1768457 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:20]=1[C:19]1[C:10](=[C:11]3[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH3:22])([CH3:21])[C:13](=[O:23])[NH:12]3)[C:9](=[O:24])[O:8]2.[C:25](=O)([O-])[O-].[Cs+].[Cs+].CI.O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:20]=1[C:19]1[C:10](=[C:11]3[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH3:22])([CH3:21])[C:13](=[O:23])[N:12]3[CH3:25])[C:9](=[O:24])[O:8]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 23614998HCID 23614998, compound

Product 1

HCID 23614997HCID 23614997, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tetracyclic lactone ix (100 mg, 0.32 mmol) in DMF (5 mL) was added cesium carbonate (263 mg, 0.81 mmol) and methyl iodide (100 μL, 1.60 mmol). The mixture was stirred at 40° C. overnight, poured into water (30 mL) and extracted with EtOAc(3×30 mL). The combined extracts were washed with brine and dried (MgSO4), the solvent was removed under reduced pressure to yield a product that was used in the next step with no further purification. A small portion of the residue was purified by reverse phase preparative HPLC for characterization. 1H NMR (acetone-d6) δ 8.69 (d, J=8.4 Hz, 1H), 7.39 (t, J=8.4 Hz, 1H), 7.31 (d, J=8.4, 1H), 7.02 (d, J=8.4, 1H), 6.94 (d, J=8.4 Hz, 1H), 6.04 (br, 1H), 4.06 (s, 3H), 3.27 (s, 3H) 1.32 (s, 6H). Anal. Calcd for C19H18N2O4⅓CF3COOH⅓H2O: C, 61.78; H, 5.01; N, 7.33. Found: C, 61.64; H, 4.84; N, 7.51.

Workup

  1. extractionextracted with EtOAc(3×30 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed under reduced pressure
  5. customto yield a product that
  6. customwas used in the next step with no further purification
  7. customA small portion of the residue was purified by reverse phase preparative HPLC for characterization

Sources & evidence

ORD record
ord-5f1df8ce167e4e26beb03c31fc473cac
Source dataset
uspto-grants-2007_06
Patent number
US07235662B2

Reaction notes

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