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

HRID 597796

反応式

HRID 597796 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3cfeb6da15b64c9a846fa6eddc2f2007
出典データセット
uspto-grants-2011_03
特許番号
US07897560B2

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