Réaction #66043

Équation de réaction

15

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

lithium hydroxide monohydrate

→

title compound

Rendement 100.0%

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

Rendement 100.0%

Solvants

water

THF water

Conditions de réaction

Traitement

1. 1
   Autrethe THF was removed by evaporation
2. 2
   ExtractionThe aqueous layer was extracted 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 organic fractions were dried
6. 6
   Autreevaporated

Mode opératoire

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.

Source