1,2-Dichloroethane → 6-[[[2-(3-Benzoylphenyl)-1-oxopropyl]amino]sulfonyl]hexanoic acid

HRID 597796

Reaction equation

HRID 597796 reaction equation
O[C:2]([CH:4]([C:6]1[CH:19]=[CH:18][CH:17]=[C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:7]=1)[CH3:5])=[O:3].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl.C([O:36][C:37](=[O:47])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][S:43](=[O:46])(=[O:45])[NH2:44])C>ClCCl>[C:9]([C:8]1[CH:7]=[C:6]([CH:4]([CH3:5])[C:2]([NH:44][S:43]([CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][C:37]([OH:47])=[O:36])(=[O:45])=[O:46])=[O:3])[CH:19]=[CH:18][CH:17]=1)(=[O:10])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 3825KetoprofenHCID 181649HOAtHCID 58871553848432-25-7

Product 1

HCID 112242106-[[[2-(3-Benzoylphenyl)-1-oxopropyl]amino]sulfonyl]hexanoic acidYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of racemic ketoprofen (3.81 g, 15.0 mmol) in dichloromethane (50 ml) were added HOAt (2.04 g, 15.0 mmol) and EDC (2.88 g, 15.0 mmol), and the mixture was stirred until a clear solution resulted. To this solution was added a solution of 6-sulfamoylhexanoic acid ethyl ester (2.23 g, 10.0 mmol) and DI PEA (2.56 ml) in dichloromethane, and the mixture was stirred at room temperature for 3 d. The mixture was washed with 1N aqueous HCl, dried over MgSO4, and concentrated. Purification by column chromatography yielded 2.0 g (44%) of the title compound. An analytical sample was obtained by preparative HPLC.

Workup

  1. customresulted
  2. stirringthe mixture was stirred at room temperature for 3 d
  3. washThe mixture was washed with 1N aqueous HCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-3cfeb6da15b64c9a846fa6eddc2f2007
Source dataset
uspto-grants-2011_03
Patent number
US07897560B2

Linked notes

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