反応 #66051

反応方程式

98

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

lithium hydroxide monohydrate

→

title compound

収率 55.0%

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

収率 55.0%

溶媒

water

THF water

反応条件

後処理

1. 1
   その他the THF was removed by evaporation
2. 2
   洗浄The aqueous layer was washed with DCM (40 mL)
3. 3
   その他to remove unreacted
4. 4
   抽出the resulting precipitate was extracted with DCM (3×40 mL)
5. 5
   その他The combined organics were dried
6. 6
   その他evaporated

実験手順

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.

出典