Ketoprofen → HCID 86623049, compound

HRID 1359994Notes

Reaction equation

HRID 1359994 reaction equation
[C:1]([C:8]([NH2:15])([OH:14])[CH2:9][CH2:10][CH2:11][CH2:12][OH:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH:16][C:17]([CH:19]([C:21]1[CH:34]=[CH:33][CH:32]=[C:23]([C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])[CH:22]=1)[CH3:20])=[O:18].CCN=C=NCCCN(C)C.Cl>ClCCl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[C:1]([C:8]([NH2:15])([OH:14])[CH2:9][CH2:10][CH2:11][CH2:12][OH:13])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2].[OH:18][C:17]([CH:19]([C:21]1[CH:34]=[CH:33][CH:32]=[C:23]([C:24]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:25])[CH:22]=1)[CH3:20])=[O:16]

Participants

7

Reactant 3

HCID 3825KetoprofenHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86623048HCID 86623048, compound

Product 1

HCID 86623049HCID 86623049, compoundYield 145.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent4×HCID 8857Ethyl AcetateSolvent

Procedure

Boc-amino-1,5-pentanediol (Boc-NHCH(CH2OH)CH2CH2CH2OH, manufactured by Aldrich Chem. Co.) (1.98 mmol) was dissolved in dichloromethane (2 ml), and a dichloromethane solution (4 ml) of ketoprofen (3.96 mmol) (manufactured by Tokyo Kasei Kogyo) and a dichloromethane solution (1 ml) of DMAP (0.791 mmol) were added thereto in this order, followed by stirring. The reaction solution was ice-cooled, and a dichloromethane solution (5 ml) of WSCI.HCl (4.93 mmol) was added thereto, followed by stirring overnight while gradually returning to room temperature. The reaction solution was diluted with ethyl acetate, washed with 5% aqueous citric acid solution, 5% aqueous sodium hydrogen carbonate solution and saturated brine consecutively, followed by dehydration drying with sodium sulfate, and then the solvent was evaporated under reduced pressure. The thus obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:2, 0.5% triethylamine) to give the titled compound (1.361 g, yield 99%). The structure was identified by 1H-NMR (CDCl3).

Workup

  1. temperaturecooled
  2. stirringby stirring overnight
  3. customwhile gradually returning to room temperature
  4. washwashed with 5% aqueous citric acid solution, 5% aqueous sodium hydrogen carbonate solution and saturated brine consecutively
  5. dry with materialdrying 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=5:2, 0.5% triethylamine)

Sources & evidence

ORD record
ord-dd218e2e9e264f6e9134ac3daa753521
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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