反应 #66051

反应方程式

98

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

lithium hydroxide monohydrate

→

title compound

收率 55.0%

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

收率 55.0%

溶剂

water

THF water

反应条件

后处理

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

实验过程

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.

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