Reaktion #1003347

Reaktionsgleichung

2-(2-methylbenzoyl)cyclohexanone

L-tyrosine methyl ester

methanol

water

→

title compound

Ausbeute 34.0%

2-[(2-(2-methylbenzoyl)phenyl)amino]-3-(4-hydroxyphenyl)-propionic acid methyl ester

Ausbeute 34.0%

Lösungsmittel

anisole

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture is heated
2. 2
   Sonstigeis removed by a Dean-Stark apparatus
3. 3
   Filtrationthe Pd/C is filtered
4. 4
   Waschenwashed with anisole (3×60 ml)
5. 5
   TemperaturThe mixture is cooled to 40° C.
6. 6
   workup.ADDITIONhexane (1000 ml) is added
7. 7
   FiltrationThe solid is filtered
8. 8
   Waschenwashed with hexane (5×200 ml)
9. 9
   Sonstigeto yield the crude 2-[(2-(2-methyl benzoyl)phenyl)-amino]-3-(4-hydroxyphenyl)-propionic acid methyl ester
10. 10
    Temperaturis refluxed for 30 min
11. 11
    TemperaturAfter cooled to 0° C.
12. 12
    Filtrationthe product is filtered
13. 13
    Waschenwashed with methanol (2×50 ml)
14. 14
    Sonstigedried under a vacuum

Vorschrift

To a mixture of 2-(2-methylbenzoyl)cyclohexanone (97.2 g, 0.45 mol), L-tyrosine methyl ester (78.0 g, 0.40 mol) in anisole (1000 ml) is added 5% palladium on carbon (20 g), then the mixture is heated to reflux for 2 h while the resulting water is removed by a Dean-Stark apparatus. The mixture is cooled to 80° C., and the Pd/C is filtered and washed with anisole (3×60 ml). The mixture is cooled to 40° C., hexane (1000 ml) is added and the mixture kept at −20° C. for 48 h. The solid is filtered and washed with hexane (5×200 ml) to yield the crude 2-[(2-(2-methyl benzoyl)phenyl)-amino]-3-(4-hydroxyphenyl)-propionic acid methyl ester. The crude product is mixed with 250 ml of methanol and is refluxed for 30 min. After cooled to 0° C., the product is filtered, washed with methanol (2×50 ml), and dried under a vacuum to give the title compound (52.9 g, 34%).

Quelle