Dimethylformamide → (RS)-Naproxen methyl ester

HRID 248581

反応式

HRID 248581 の反応式
C1(C)C=CC(S(O[CH:11](C)[C:12](OC)(OC)[C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=3)[CH:14]=2)(=O)=O)=CC=1.[CH3:31]S(OC(C)C(OC)(OC)C1C=CC2C(=CC=C(OC)C=2)C=1)(=O)=O.[C:55](=[O:58])([O-])[O-:56].[Ca+2].CN(C)C=O>O>[CH3:24][O:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([CH:12]([CH3:11])[C:55]([O:56][CH3:31])=[O:58])[CH:22]=[CH:21]2

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 10112Calcium CarbonateHCID 127563301,1-Dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonateHCID 200291641,1-Dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl p-toluenesulfonate

生成物 1

HCID 529084(RS)-Naproxen methyl ester

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 3.07 grams of (S) 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate, 1.0 gram of calcium carbonate, 100 ml. of dimethylformamide and 25 ml. of water is heated to 110° C. and maintained at that temperature for 5 hours. Then the mixture is cooled and the insolubles removed by filtration. The filtrate is poured into excess water and the solid which forms is collected by filtration. Separation by chromatography yields methyl 2-(6-methoxy-2-naphthyl)propionate, exhibiting an [α]25D =77° in chloroform and an optical purity of greater than 99 percent.

後処理

  1. temperaturemaintained at that temperature for 5 hours
  2. temperatureThen the mixture is cooled
  3. customthe insolubles removed by filtration
  4. additionThe filtrate is poured into excess water
  5. filtrationthe solid which forms is collected by filtration
  6. customSeparation by chromatography

出典と根拠

ORDレコード
ord-85dfc98f0b7542c996060eccd1aa2431
出典データセット
uspto-grants-1993_05
特許番号
US05210258

関連ノート

読み込み中…