Reaction #66051

Reaction equation

98

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

lithium hydroxide monohydrate

→

title compound

Yield 55.0%

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

Yield 55.0%

Solvents

water

THF water

Conditions

Workup

1. 1
   Otherthe THF was removed by evaporation
2. 2
   WashThe aqueous layer was washed with DCM (40 mL)
3. 3
   Otherto remove unreacted
4. 4
   Extractionthe resulting precipitate was extracted with DCM (3×40 mL)
5. 5
   OtherThe combined organics were dried
6. 6
   Otherevaporated

Procedure

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