Mefenamic acid → HCID 86623038, compound

HRID 1359985Notes

Reaction equation

HRID 1359985 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].[CH3:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([NH:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=2[C:28]([OH:30])=[O:29])[C:19]=1[CH3:20].CCN=C=NCCCN(C)C.Cl.C(OCC)(=O)C>CN(C1C=CN=CC=1)C.ClCCl>[C:6]([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7].[CH3:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([NH:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=2[C:28]([OH:30])=[O:29])[C:19]=1[CH3:20]

Participants

7

Reactant 4

HCID 4044Mefenamic acidHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 23149331t-Butoxycarbonyl-aminopropanol

Product 1

HCID 86623038HCID 86623038, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

Boc-aminopropanol (0.616 mmol), mefenamic acid (0.620 mmol) (manufactured by Wako Pure Chemical Industries) and DMAP (0.126 mmol) were dissolved in dichloromethane (3 ml), and a dichloromethane solution (1.5 ml) of WSCI.HCl (0.758 mmol) was added thereto, under ice-cooling. After gradually returning the reaction temperature to room temperature, the mixture was stirred overnight. The reaction solution was again ice-cooled, and a dichloromethane solution (1 ml) of WSCI.HCl (0.207 mmol) was added thereto, followed by stirring for 5 hours while gradually returning to room temperature. Ethyl acetate was added to the reaction solution, and the mixture was washed 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=6:1, 0.5% triethylamine) to give the titled compound (190.4 mg, yield 78%). The structure was identified by 1H-NMR (CDCl3).

Workup

  1. temperatureunder ice-cooling
  2. customto room temperature
  3. temperaturecooled
  4. stirringby stirring for 5 hours
  5. customwhile gradually returning to room temperature
  6. washthe mixture was washed with 5% aqueous citric acid solution, 5% aqueous sodium hydrogen carbonate solution and saturated brine consecutively
  7. dry with materialAfter dehydration drying with sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe thus obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1, 0.5% triethylamine)

Sources & evidence

ORD record
ord-1a10515e7ad640899f763d332664dc58
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

Loading…