تفاعل #66043

معادلة التفاعل

15

Ethyl (2S)-2-acetamido-3-(4-allyloxyphenyl)propanoate

lithium hydroxide monohydrate

→

title compound

المردود 100.0%

(2S)-2-Acetamido-3-(4-allyloxyphenyl)propanoic acid

المردود 100.0%

المذيبات

water

THF water

ظروف التفاعل

المعالجة

1. 1
   أخرىthe THF was removed by evaporation
2. 2
   استخلاصThe aqueous layer was extracted with DCM (40 mL)
3. 3
   أخرىto remove unreacted
4. 4
   استخلاصthe resulting precipitate was extracted with DCM (3×40 mL)
5. 5
   أخرىThe combined organic fractions were dried
6. 6
   أخرىevaporated

الإجراء التجريبي

To a solution of 15 (2.90 g, 9.98 mmol) in THF/water, (3:1, 80 mL) was added lithium hydroxide monohydrate (838 mg, 20.0 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 extracted 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 organic fractions were dried and evaporated to yield the title compound (2.62 g, 9.98 mmol, 100%) as white needles, which had spectral data in agreement with that reported.122 Mp 170-172° C. (lit 200° C.)122 1H NMR (D6 acetone, 300 MHz): δ 7.09 (s, 1H, NH); 7.04 (d, J=8.4 Hz, 2H, ArH2′ and ArH6′); 6.73 (d, J=8.4 Hz, 2H, ArH3′ and ArH5′); 5.94 (m, 1H, H2″); 5.27 (dd J=1.3 Hz, 17.3 Hz, 1H, H3a″); 5.10 (dd J=1.3, 10.5 Hz, 1H, H3b″); 4.52 (m, 1H, H2); 4.41 (d J=5.5 Hz, 2H, H1″); 2.98 (dd, J=5.7, 14.1 Hz, 2H, H3a); 2.79 (dd, J=8.1, 14.1 Hz, 2H, H3b); 1.75 (s, 3H, NCOCH3). Mass Spectrum (CI, +ve) m/z 264 (100%) [MH+]. HRMS calcd for C14H18NO4 264.1236, found 264.1246.

المصدر