Fenbufen → HCID 86623036, compound

HRID 1359983Notes

Reaction equation

HRID 1359983 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].[CH:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])=[CH:23][CH:24]=2)=[CH:17][CH:18]=1.ClCCl.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C.ClCCl.C(OCC)(=O)C>[C:6]([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7].[CH:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])=[CH:23][CH:24]=2)=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 3335FenbufenHCID 6344DichloromethaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23149331t-Butoxycarbonyl-aminopropanol

Product 1

HCID 86623036HCID 86623036, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

Boc-aminopropanol (2.18 mmol), fenbufen (2.18 mmol) (manufactured by ICN Biochemicals Inc.) and DMAP (0.44 mmol) were dissolved in DMF-dichloromethane (5:3, 8 ml), and dichloromethane solution (5 ml) of WSCI.HCl (2.48 mmol) was added thereto under ice-cooling. After gradually returning the reaction temperature to room temperature, the mixture was stirred 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 (chloroform:ethyl acetate=40:1, 0.5% triethylamine) to give the titled compound (747.8 mg, yield 83%). The structure was identified by 1H-NMR (CDCl3).

Workup

  1. temperatureunder ice-cooling
  2. customto 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 (chloroform:ethyl acetate=40:1, 0.5% triethylamine)

Sources & evidence

ORD record
ord-7a677bca2c8147919bab7a69f44ba6b6
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

Loading…