Felbinac → HCID 86623034, compound

HRID 1359981Notes

Reaction equation

HRID 1359981 reaction equation
[C:1]([O:5][C:6]([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:13][C:14]([CH2:16][C:17]1[CH:28]=[CH:27][C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:19][CH:18]=1)=[O:15].O1CCOCC1.ClCCl.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.O1CCOCC1.C(OCC)(=O)C.CN(C)C=O>[C:6]([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7].[OH:15][C:14]([CH2:16][C:17]1[CH:28]=[CH:27][C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:19][CH:18]=1)=[O:13]

Participants

9

Reactant 4

HCID 3332FelbinacHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18626912Dioxane methylene chlorideHCID 23149331t-Butoxycarbonyl-aminopropanol

Product 1

HCID 86623034HCID 86623034, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Boc-aminopropanol (2.04 mmol), felbinac (2.04 mmol) (manufactured by Aldrich Chem. Co.) and DMAP (0.41 mmol) were dissolved in dioxane (7 ml) and then a dioxane-dichloromethane (3:4) solution (7 ml) of WSCI.HCl (2.35 mmol) was added thereto under ice-cooling. The reaction solution was clarified by adding dimethylformamide (DMF) (3 ml) and then returned to room temperature, followed by stirring overnight. Ethyl acetate was added thereto, followed by separation by washing with 5% aqueous citric acid solution, 5% aqueous sodium hydrogen carbonate solution and saturated brine consecutively. After dehydration drying with sodium sulfate, the solvent was evaporated under reduced pressure. The thus obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1, 0.5% triethylamine) to give the titled compound (623.0 mg, yield 83%). The structure was identified by 1H-NMR (CDCl3).

Workup

  1. temperatureunder ice-cooling
  2. customreturned to room temperature
  3. customfollowed by separation
  4. washby washing with 5% aqueous citric acid solution, 5% aqueous sodium hydrogen carbonate solution and saturated brine consecutively
  5. dry with materialAfter dehydration drying with sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe thus obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1, 0.5% triethylamine)

Sources & evidence

ORD record
ord-489baa431aae40798fc8cbccdd4962c8
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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