Réaction #66051

Équation de réaction

98

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

lithium hydroxide monohydrate

→

title compound

Rendement 55.0%

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

Rendement 55.0%

Solvants

water

THF water

Conditions de réaction

Traitement

1. 1
   Autrethe THF was removed by evaporation
2. 2
   LavageThe aqueous layer was washed with DCM (40 mL)
3. 3
   Autreto remove unreacted
4. 4
   Extractionthe resulting precipitate was extracted with DCM (3×40 mL)
5. 5
   AutreThe combined organics were dried
6. 6
   Autreevaporated

Mode opératoire

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.

Source