Hydrochloric Acid → HCID 23156210, compound

HRID 1890646Notes

Reaction equation

HRID 1890646 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][NH:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:24]5=[N:25][C:26]([CH3:30])=[CH:27][C:28]([CH3:29])=[C:23]5[N:22]=[C:21]4[CH2:31][CH3:32])=[CH:15][CH:14]=3)[CH2:7][CH2:6]2)[O:4]CC1.Cl.[OH-].[Na+]>C1COCC1>[CH2:31]([C:21]1[N:20]([CH2:19][C:16]2[CH:15]=[CH:14][C:13]([NH:12][CH2:11][CH:8]3[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]3)=[CH:18][CH:17]=2)[C:24]2=[N:25][C:26]([CH3:30])=[CH:27][C:28]([CH3:29])=[C:23]2[N:22]=1)[CH3:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69433831HCID 69433831, compound

Product 1

HCID 23156210HCID 23156210, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 144 (488 mg, 1.12 mmol) was dissolved in THF (7.4 mL), and 5% hydrochloric acid (3.7 mL) was added to the solution, followed by stirring at room temperature for 9 hours. The reaction mixture was added with a 2 mol/L aqueous sodium hydroxide solution and extracted with ethyl acetate three times. 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=1:19). The desired compound was recrystallized from diethyl ether to obtain Compound 148 (360 mg, 0.922 mmol, 82.1%).

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methanol:chloroform=1:19)
  6. customThe desired compound was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-7aa92778b6fb4c03a3669d399d469044
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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