Water → HCID 23614998, compound

HRID 1768456Notes

Reaction equation

HRID 1768456 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:19]=1[C:18]1[C:9](=[C:10]3[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH3:21])([CH3:20])[C:12](=[O:22])[NH:11]3)[C:8](=[O:23])[O:7]2.[C:24](=O)([O-])[O-].[Cs+].[Cs+].CI.O>CN(C=O)C>[CH3:24][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:19]=1[C:18]1[C:9](=[C:10]3[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH3:21])([CH3:20])[C:12](=[O:22])[NH:11]3)[C:8](=[O:23])[O:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 23614996HCID 23614996, compound

Product 1

HCID 23614998HCID 23614998, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of phenol viii (200 mg, 0.65 mmol) in DMF (10 mL) was added cesium carbonate (419 mg, 1.29 mmol) and methyl iodide (88 μL, 1.42 mmol). The mixture was stirred at room temperature for 1 h and then poured into cold water (50 mL). The mixture was then extracted with EtOAc (5×50 mL). The combined extracts were washed with brine and dried (MgSO4). The solvent was removed under reduced pressure to provide the crude tetracyclic lactone ether ix (163 mg) as a yellow solid that was used in the next step without further purification. A small portion of the crude ix was purified by reverse phase preparative HPLC for characterization. 1H NMR (acetone-d6) δ 10.90 (br s, 1H), 8.59 (d, J=8.4, 1H), 7.34 (t, J=8.4 Hz, 1H), 7.21 (d, J=8.4, 1H), 6.98 (d, J=8.4, 1H), 6.90 (d, J=8.4 Hz, 1H), 5.93 (br s, 1H), 4.01 (s, 3H), 1.34 (s, 6H). Anal. Calcd for C18H16N2O4: C, 66.66; H, 4.97; N, 8.64. Found: C, 66.66; H, 4.79; N, 8.96.

Workup

  1. extractionThe mixture was then extracted with EtOAc (5×50 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4d16f6e4f08449488e609729eaeb07d4
Source dataset
uspto-grants-2007_06
Patent number
US07235662B2

Reaction notes

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