Sodium hydride → HCID 54045762, compound

HRID 1739663Notes

Reaction equation

HRID 1739663 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][C:17]1[C:22]([Cl:23])=[CH:21][C:20]([C:24]([OH:26])=[O:25])=[CH:19][N:18]=1)[C:5]([NH:7][CH3:8])=[O:6].C(N1C=CN=C1)(N1C=CN=C1)=O.[H-].[Na+].[C:41]([O:57][CH2:58][CH3:59])(=[O:56])[C:42]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)O.[N-]1C=CN=C1>C1COCC1.O>[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][C:17]1[C:22]([Cl:23])=[CH:21][C:20]([C:24]([O:26][C:42]([C:41]([O:57][CH2:58][CH3:59])=[O:56])([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:25])=[CH:19][N:18]=1)[C:5]([NH:7][CH3:8])=[O:6]

Participants

8

Reactant 5

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 96261Ethyl diphenylglycolateHCID 3386966ImidazolateHCID 53726168HCID 53726168, compound

Product 1

HCID 54045762HCID 54045762, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The product of Example 38 (0.5 g, 1.32 mmol) was dissolved in 15 mL THF to which was added carbonyldiimidazole (0.24 g, 1.48 mmol). The solution was stirred at room temperature for one hour. NaH (60% dispersion in mineral oil, 0.08 g, 3.2mmol) was washed (2×) with hexanes then suspended in THF (10 mL) to which was added ethyl benzilate (0.40 g, 3.2 mmol). After 20 minutes, the imidazolide intermediate was added dropwise to the solution of alcoholic anion and stirring continued at room temperature overnight. The solution was poured into 4-5 volumes of water and extracted with Et2O (2×100 mL). The organics were dried over MgSO4 and concentrate to a yellow oil (0.60 g). Product was chromatographed on medium column using silica gel (230-400 mesh) with isocratic 80/20 petroleum ether/ethyl acetate as the mobile phase. Elution and concentration gave α-(methoxyimino)-N-methyl-2-[[[3-chloro-5-(ethoxycarbonyldiphenylmethoxycarbonyl)-2-pyridinyl]oxy]methyl]-benzeneacetamide (0.50 g) as a yellow solid.

Workup

  1. waitAfter 20 minutes
  2. stirringstirring
  3. waitcontinued at room temperature overnight
  4. extractionextracted with Et2O (2×100 mL)
  5. dry with materialThe organics were dried over MgSO4
  6. concentrationconcentrate to a yellow oil (0.60 g)
  7. customProduct was chromatographed on medium column
  8. washElution and concentration

Sources & evidence

ORD record
ord-2a02d57567ba4cde88cdd1df9efd57f8
Source dataset
uspto-grants-1999_10
Patent number
US05968875

Reaction notes

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