Dimethylformamide → (RS)-Naproxen methyl ester

HRID 579895

Reaktionsgleichung

Reaktionsgleichung von HRID 579895
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

Komponenten

6

Edukt 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

Produkt 1

HCID 529084(RS)-Naproxen methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ae768195c6c6489887e7164d2547b240
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04749804

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