Etodolac → HCID 86623041, compound

HRID 1359988Notes

Reaction equation

HRID 1359988 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][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]3[CH2:24][CH2:25][O:26][C:27]([CH2:30][C:31]([OH:33])=[O:32])([CH2:28][CH3:29])[C:22]=3[NH:21][C:20]=12.CCN=C=NCCCN(C)C.Cl.C(OCC)(=O)C>ClCCl.CN(C1C=CN=CC=1)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].[CH3:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]3[CH2:24][CH2:25][O:26][C:27]([CH2:30][C:31]([OH:33])=[O:32])([CH2:28][CH3:29])[C:22]=3[NH:21][C:20]=12

Participants

7

Reactant 4

HCID 3308EtodolacHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 23149331t-Butoxycarbonyl-aminopropanol

Product 1

HCID 86623041HCID 86623041, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

In 4 ml of dichloromethane, 178.8 mg (1.02 mmol) of Boc-aminopropanol, 293.8 mg (1.02 mmol) of etodolac (manufactured by Wako Pure Chemical Industries) and 23.8 mg (0.20 mmol) of DMAP were dissolved, and 2 ml dichloromethane solution of 233.8 mg (1.22 mmol) WSCI.HCl was added thereto under ice-cooling, followed by stirring overnight while gradually returning to room temperature. Further under ice-cooling, 2 ml dichloromethane solution of 68.8 mg (0.36 mmol) WSCI.HCl was added thereto, followed by stirring for 80 minutes while gradually returning to room temperature. Ethyl acetate was added thereto, followed by separation by washing twice with 5% aqueous citric acid solution, twice with 5% aqueous sodium hydrogen carbonate solution and with saturated brine consecutively. After dehydration drying with sodium sulfate, ethyl acetate was evaporated under reduced pressure. The thus obtained residue was purified by silica gel column chromatography to give 436.3 mg (96%) of the titled compound. The structure was identified by 1H-NMR.

Workup

  1. temperatureunder ice-cooling
  2. customwhile gradually returning to room temperature
  3. temperatureFurther under ice-cooling
  4. stirringby stirring for 80 minutes
  5. customwhile gradually returning to room temperature
  6. customfollowed by separation
  7. washby washing twice with 5% aqueous citric acid solution, twice with 5% aqueous sodium hydrogen carbonate solution and with saturated brine consecutively
  8. dry with materialAfter dehydration drying with sodium sulfate, ethyl acetate
  9. customwas evaporated under reduced pressure
  10. customThe thus obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b13343f543254b9d863f12ff583b0598
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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