Sodium Hydroxide → HCID 178437434, compound

HRID 1890648Notes

Reaction equation

HRID 1890648 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][CH2:32][CH:33]3[CH2:38][CH2:37][C:36](=[O:39])[CH2:35][CH2:34]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+]>C1COCC1>[CH2:11]([C:13]1[N:23]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([NH:31][CH2:32][C@H:33]3[CH2:34][CH2:35][C@H:36]([OH:39])[CH2:37][CH2:38]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

6

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 23156210HCID 23156210, compound

Product 1

HCID 178437434HCID 178437434, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Lithium aluminum hydride (23.3 mg, 0.616 mmol) was suspended in THF (0.6 mL), and a solution of aluminum chloride (41.1 mg, 0.308 mmol) in THF (0.6 mL) was added to the suspension at 0° C., followed by stirring for 5 minutes. Then the mixture was added with a solution of Compound 148 (60.0 mg, 0.154 mmol) in THF (1.4 mL) followed by stirring at 0° C. for 0.5 hours. The reaction mixture was added with 2 mol/L aqueous sodium hydroxide solution and extracted with ethyl acetate twice. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol:chloroform=1:49). The obtained compound was crystallized from diethyl ether to obtain Compound 152 (cis:trans=15:85, 38.1 mg, 0.0971 mmol, 63.2%).

Workup

  1. stirringby stirring at 0° C. for 0.5 hours
  2. extractionextracted with ethyl acetate twice
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methanol:chloroform=1:49)
  7. customThe obtained compound was crystallized from diethyl ether

Sources & evidence

ORD record
ord-158ebb2b657541dab4cce7d087753df3
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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