Dimethylformamide → (RS)-Naproxen methyl ester

HRID 248581

반응식

HRID 248581 반응식
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

참가 물질

6

반응물 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

생성물 1

HCID 529084(RS)-Naproxen methyl ester

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-85dfc98f0b7542c996060eccd1aa2431
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05210258

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