Tetrahydrofuran → HCID 131723021, compound

HRID 2270097Notes

Reaction equation

HRID 2270097 reaction equation
[H-].[Na+].O1CCCC1.[CH3:8][O:9][C:10]([N:12]1[CH2:16][CH2:15][CH:14]([NH:17][CH:18]=[C:19]([C:25](=[O:33])[C:26]2[CH:31]=[CH:30][CH:29]=[N:28][C:27]=2Cl)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13]1)=[O:11]>O>[CH3:8][O:9][C:10]([N:12]1[CH2:16][CH2:15][CH:14]([N:17]2[C:27]3[C:26](=[CH:31][CH:30]=[CH:29][N:28]=3)[C:25](=[O:33])[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18]2)[CH2:13]1)=[O:11]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 178471952HCID 178471952, compound

Product 1

HCID 131723021HCID 131723021, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

45 mg of sodium hydride (abt. 60% oil suspension 1.13 mmol) was added to 5 ml of a tetrahydrofuran solution of 411 mg of the compound obtained in Example 1 (1.08 mmol) under an argon atmosphere at 0° C. and the solution was stirred at the same temperature for 5 minutes. It was further stirred at room temperature for 30 minutes, then water (15 ml) was added and extraction was performed with ethyl acetate (30 ml). Next, the organic layer was washed with saturated saline (10 ml), then dried over anhydrous sodium sulfate, then the solvent was distilled off under vacuum. The precipitated crystal was washed with diethyl ether and the crystal was obtained by filtration to obtain 314 mg (84%) of the above-identified compound as a colorless crystal.

Workup

  1. stirringIt was further stirred at room temperature for 30 minutes
  2. extractionextraction
  3. washNext, the organic layer was washed with saturated saline (10 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under vacuum
  6. washThe precipitated crystal was washed with diethyl ether
  7. customthe crystal was obtained by filtration

Sources & evidence

ORD record
ord-acb23c9d6b29451696d16c91c7c89bdf
Source dataset
uspto-grants-2001_12
Patent number
US06331548B1

Reaction notes

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