Reacción #66051

Ecuación de reacción

98

Methyl (2S)-2-acetamido-3-(4-[9-phenanthrenyl]phenyl)propanoate

lithium hydroxide monohydrate

→

title compound

Rendimiento 55.0%

(2S)-2-Acetamido-3-(4-[9-phenanthrenyl]phenyl)propanoic acid

Rendimiento 55.0%

Disolventes

water

THF water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe THF was removed by evaporation
2. 2
   LavadoThe aqueous layer was washed with DCM (40 mL)
3. 3
   Otroto remove unreacted
4. 4
   Extracciónthe resulting precipitate was extracted with DCM (3×40 mL)
5. 5
   OtroThe combined organics were dried
6. 6
   Otroevaporated

Procedimiento

To a solution of 98 (124 mg, 0.31 mmol) in THF/water, 2:1 (9 mL) was added lithium hydroxide monohydrate (26 mg, 0.62 mmol) and the resulting suspension was allowed to stir for 16 h. The reaction mixture was diluted with water (30 mL) and the THF was removed by evaporation. The aqueous layer was washed with DCM (40 mL) to remove unreacted starting material. The aqueous phase was acidified with 10% HCl and the resulting precipitate was extracted with DCM (3×40 mL). The combined organics were dried and evaporated to yield the title compound (65 mg, 0.17 mmol, 55%) as a white solid. Mp 128-132° C. [α]D20+36.8 (c. 0.1, EtOH). 1H NMR (CD3OD, 300 MHz): δ 8.71 (d, J=8.1 Hz, 1H, ArH4″); 8.66 (d, J=8.4 Hz, 1H, ArH3″); 7.79 (s, 1H, ArH1″); 7.76 (s, 1H, ArH10″); 7.51 (m, 5H, ArH7″, ArH6″, ArH5″, ArH2″ and ArH1″); 7.32 (m, 2H, Ar′H); 4.76 (dd, J=5.1, 9.0 Hz, 1H, H2); 3.29 (dd, J=4.8, 13.5 Hz, 1H, H3a); 3.03 (dd, J=8.7, 13.5 Hz, 1H, H3b); 1.95 (s, 3H, COCH3). Mass Spectrum (ES, +ve) m/z 384 (50%) [MH+]. HRMS calcd for C25H22NO3 384.1600, found 384.1628.

Fuente