Hydrochloric Acid → HCID 68814486, compound

HRID 732508Notes

Reaction equation

HRID 732508 reaction equation
C(O[C:4](=[O:20])[C:5]1[CH:15]=[C:14]([CH:16]=[C:17]([CH3:19])[CH3:18])[CH:13]=[C:7]([C:8]([O:10]CC)=[O:9])[CH:6]=1)C.[OH-].[Na+].Cl.[CH3:24][N:25](C)[CH2:26][CH2:27][CH2:28]N=C=NCC.ON1C2C=CC=CC=2N=N1.CNCCC.C(N(CC)CC)C.[OH-].[Li+].Cl>CC(C)=O.CO.CN(C=O)C.C(OCC)(=O)C>[CH3:24][N:25]([CH2:26][CH2:27][CH3:28])[C:4](=[O:20])[C:5]1[CH:6]=[C:7]([CH:13]=[C:14]([CH:16]=[C:17]([CH3:18])[CH3:19])[CH:15]=1)[C:8]([OH:10])=[O:9]

Participants

13

Reactant 8

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 12315N-MethylpropylamineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68817821HCID 68817821, compound

Product 1

HCID 68814486HCID 68814486, compoundYield 41.2%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 5-(2-methylpropenyl)-isophthalic acid diethyl ester (535 mg, 1.94 mmol) in acetone (10 mL) and add a solution of NaOH (77 mg, 1.94 mmol) in methanol (2 mL). Stir at room temperature 2 days and concentrate. Dissolve in water and wash with diethyl ether. Acidify the water layer to about pH=1 with 1 N HCl and extract with dichloromethane. Dry the dichloromethane layer over magnesium sulfate, filter and concentrate. Dissolve the residue in DMF (10 mL) and add 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride (409 mg, 2.13 mmol) and 1-hydroxybenzotriazole (288 mg, 2.13 mmol). After 30 min, add methyl-propyl-amine (283 mg, 3.87 mmol) and triethylamine (665 mg, 6.58 mmol) in DMF (2 mL). Stir at room temperature 1 h and dilute with ethyl acetate. Wash with 10% aqueous potassium carbonate, 0.1 N citric acid, 1 N lithium chloride and saturated aqueous sodium chloride and concentrate. Dissolve the residue in THF (20 mL) and add 1 N lithium hydroxide (10 mL, 10 mmol). Stir at room temperature for 4 h and acidify to about pH=1 with 1 N HCl. Extract with dichloromethane, dry (magnesium sulfate), filter and concentrate to give the title compound as a solid (220 mg, 41%).

Workup

  1. concentrationconcentrate
  2. dissolutionDissolve in water
  3. washwash with diethyl ether
  4. extractionextract with dichloromethane
  5. dry with materialDry the dichloromethane layer over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. dissolutionDissolve the residue in DMF (10 mL)
  9. waitAfter 30 min
  10. stirringStir at room temperature 1 h
  11. washWash with 10% aqueous potassium carbonate, 0.1 N citric acid, 1 N lithium chloride and saturated aqueous sodium chloride
  12. concentrationconcentrate
  13. dissolutionDissolve the residue in THF (20 mL)
  14. stirringStir at room temperature for 4 h
  15. extractionExtract with dichloromethane
  16. dry with materialdry (magnesium sulfate)
  17. filtrationfilter
  18. concentrationconcentrate

Sources & evidence

ORD record
ord-569b2f7ae5114c1b94c86af27891becc
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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