Sodium Hydroxide → HCID 178437435, compound

HRID 1890640Notes

Reaction equation

[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C@H:22]3[CH2:27][CH2:26][C@H:25]([C:28]([N:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]4)=O)[CH2:24][CH2:23]3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>C1COCC1>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21][C@H:22]3[CH2:23][CH2:24][C@H:25]([CH2:28][N:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]4)[CH2:26][CH2:27]3)=[CH:19][CH:20]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 107t (0.0572 g, 0.117 mmol) was dissolved in THF (1.1 mL), and a solution of lithium aluminum hydride (0.0178 g, 0.468 mmol) and aluminum chloride (0.0312 g, 0.234 mmol) in THF (3.0 mL) was added to the solution, 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 chloroform three times. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from diisopropyl ether to obtain Compound 108t (0.0426 g, 0.0897 mmol, yield 77%).

Workup

extractionextracted with chloroform three times
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record: ord-cf4f8e9af8e04d0eac3c1674dcf182df
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507484B2

Reaction notes

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