Sodium Hydroxide → HCID 86615034, compound

HRID 1890639Notes

Reaction equation

HRID 1890639 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:11]([C:13]1[N:23]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]([N:40]4[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]4)=O)=[CH:34][CH:33]=3)=[CH:27][CH:26]=2)[C:16]2=[N:17][C:18]([CH3:22])=[CH:19][C:20]([CH3:21])=[C:15]2[N:14]=1)[CH3:12].[OH-].[Na+].C(O)(=O)/C=C/C(O)=O>C1COCC1>[CH2:11]([C:13]1[N:23]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([CH2:38][N:40]4[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]4)=[CH:34][CH:33]=3)=[CH:29][CH:30]=2)[C:16]2=[N:17][C:18]([CH3:22])=[CH:19][C:20]([CH3:21])=[C:15]2[N:14]=1)[CH3:12]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 69437621HCID 69437621, compound

Product 1

HCID 86615034HCID 86615034, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

Lithium aluminum hydride (0.044 g, 1.16 mmol) was suspended in THF (5.0 mL), and a solution of aluminum chloride (0.0773 g, 0.580 mmol) in THF (7.0 mL) was added to the suspention at 0° C., followed by stirring at same temperature for 10 minutes. Then, a solution of Compound 100 (0.140 g, 0.290 mmol) in THF (6.0 mL) was slowly added to the mixture, followed by stirring at 0° C. for 15 minutes. The reaction mixture was added with a 2 mol/L aqueous sodium hydroxide solution, and extracted with dichloromethane three times. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in THF, and a solution of fumaric acid (74 mg, 0.58 mmol) in THF (2 mL) was added to the solution. The precipitates were collected by filtration, and sequentially washed with THF and ethyl acetate to obtain Compound 102 (0.173 g, 0.247 mmol, yield 85%).

Workup

  1. stirringby stirring at 0° C. for 15 minutes
  2. extractionextracted with dichloromethane three times
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in THF
  6. filtrationThe precipitates were collected by filtration
  7. washsequentially washed with THF and ethyl acetate

Sources & evidence

ORD record
ord-30b0daf678744c2483a4d2e22b3d0281
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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