Dimethylformamide → (RS)-Naproxen methyl ester

HRID 579895

Reaction equation

HRID 579895 reaction equation
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

Participants

6

Reactant 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

Product 1

HCID 529084(RS)-Naproxen methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ae768195c6c6489887e7164d2547b240
Source dataset
uspto-grants-1988_06
Patent number
US04749804

Linked notes

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