Reaktion #66046

Reaktionsgleichung

52

Methyl (2R)-2-acetamido-3-(4-allyloxyphenyl)propanoate

lithium hydroxide monohydrate

→

title compound

Ausbeute 88.0%

(2R)-2-Acetamido-3-(4-Allyloxyphenyl)propanoic acid

Ausbeute 88.0%

Lösungsmittel

water

THF water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe THF was removed in vacuo
2. 2
   ExtraktionThe aqueous layer was extracted with diethyl ether (40 mL)
3. 3
   Sonstigeto remove unreacted
4. 4
   Extraktionthe resulting precipitate was extracted with DCM (3×40 mL)
5. 5
   TrocknenThe combined DCM fractions were dried
6. 6
   Sonstigeevaporated

Vorschrift

To a solution of 52 (900 mg, 3.25 mmol) in THF/water, 3:1 (10 mL) was added lithium hydroxide monohydrate (273 mg, 6.5 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 in vacuo. The aqueous layer was extracted with diethyl ether (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 DCM fractions were dried and evaporated to yield the title compound (750 mg, 2.85 mmol, 88%) as a white solid. [α]D23 −23.2 (c. 0.1, EtOH). Mp 75° C. 1HNMR (D6 acetone, 300 MHz): δ 7.27 (d, J=7.8 Hz, 1H, NH); 7.17 (d, J=8.7 Hz, 2H, ArH2′ and ArH6′); 6.86 (d, J=8.7 Hz, 21H, ArH3′ and ArH5′); 6.06 (m, 1H, H2″); 5.40 (dd J=1.5 Hz, 17.5 Hz, 1H, H3a″); 5.23 (dd, J=1.5, 10.5 Hz, 1H, H3b″); 4.67 (dd, J=5.1, 8.1, 10.5 Hz 1H, H2); 4.53 (d, J=5.1 Hz, 2H, H1″); 3.11 (dd, J=5.4, 14.1 Hz, 1H; 3Ha); 2.93 (dd, J=8.1, 14.1, 1H, 3Hb); 1.89 (s, 31H, NCOCH3). Mass Spectrum (CI, +ve) m/z 264 (100%) [MH+]. HRMS calcd for C14H18NO4 264.123583, found 264.123770.

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