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

HRID 597796

반응식

HRID 597796 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3cfeb6da15b64c9a846fa6eddc2f2007
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897560B2

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