Water → HCID 12149030, compound

HRID 585534Notes

Reaction equation

HRID 585534 reaction equation
[H-].[Na+].[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C@H:25]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20][CH:19]=1.[CH3:40]I.O>O1CCCC1>[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C@H:25]([N:31]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[CH3:40])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12149023HCID 12149023, compound

Product 1

HCID 12149030HCID 12149030, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon atmosphere, 60% sodium hydride (30 mg) was added at 0° C. to a solution of Compound 1 (253.8 mg) in tetrahydrofuran (5 mL), and the mixture was stirred for 30 minutes at room temperature. Under cooling with ice, methyl iodide (0.16 mL) was added thereto, and the resultant mixture was stirred for 88 hours at room temperature. Water was added to the reaction mixture, and the solvent was distilled off. The residue was subjected to extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the resultant crude product was subjected to purification through silica gel column chromatography (ethyl acetate-hexane=1:4 to 1:2), to thereby yield 139.3 mg of the title compound as a colorless oil.

Workup

  1. additionwas added
  2. distillationthe solvent was distilled off
  3. extractionThe residue was subjected to extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe resultant crude product was subjected to purification through silica gel column chromatography (ethyl acetate-hexane=1:4 to 1:2)

Sources & evidence

ORD record
ord-0503f4689a8a47b5b098de86eedccd92
Source dataset
uspto-grants-2005_08
Patent number
US06933309B2

Reaction notes

Loading…