Dimethylcarbamoyl Chloride → Dimethylcarbamoyloxy-phenyl-acetic acid

To hydroxyl-phenyl-acetic acid methyl ester (500 mg) in THF (10 mL) were added dimethylcarbamoyl chloride (304 μl), TEA (503 μl), and DMAP (37 mg). After stirring for overnight at room temperature, the mixture was taken up in ethyl acetate (150 mL). The organic phase was washed with 1 N HCl (1×100 mL) and saturated sodium bicarbonate (1×100 mL), and dried over sodium sulfate. After the solvent was removed, the resulting solid was dissolved in THF (6 mL). To the solution was added 2 M LiOH (3 mL). After stirring for 90 min. at room temperature, the reaction mixture was acidified with 2 N HCl (3.2 mL). The mixture was extracted with ethyl acetate (50 mL). The organic phase was dried over sodium sulfate. The solvent was removed under reduced pressure to provide dimethylcarbamoyloxy-phenyl-acetic acid (561 mg, 83%) as an off-white solid.

1. washThe organic phase was washed with 1 N HCl (1×100 mL) and saturated sodium bicarbonate (1×100 mL)
2. dry with materialdried over sodium sulfate
3. customAfter the solvent was removed
4. dissolutionthe resulting solid was dissolved in THF (6 mL)
5. additionTo the solution was added 2 M LiOH (3 mL)
6. stirringAfter stirring for 90 min. at room temperature
7. extractionThe mixture was extracted with ethyl acetate (50 mL)
8. dry with materialThe organic phase was dried over sodium sulfate
9. customThe solvent was removed under reduced pressure

ORD-Eintrag

ord-5e258357aa4a431ab1f8f83b99de4c2d

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08822430B2