3-AMINO-3-(2-METHOXYPHENYL)PROPIONIC AC& synthesis

Yield:3334-66-5 100%

Reaction Conditions:

with ethanol;potassium hydroxide in ethanol at 20; for 2.5 h;

Steps:

3-[(2-Methoxyphenyl)amino]propanoic acid (1-211)

To a stirred solution of methyl 3-[(2-methoxyphenyl)amino]propanoate (1-210) (301 mg, 1.44 mmol) in EtOH (5 ml_) was added 2M KOH (1.1 ml_, 2.16 mmol) and the reaction was stirred at RT for 2.5 h. The mixture was acidified with 1 M HCI to pH 1-2 and the aqueous layer was extracted with 1 :1 IPA/CHC (3 x 25 ml_). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to afford 349 mg of 3-[(2-methoxyphenyl)amino]propanoic acid as a grey glassy solid (100% purity, quantitative) used in the next step without further purification. 1 H NMR (250 MHz, DMSO-d6) δ 2.59 (t, J = 6.9 Hz, 2H), 3.35 (t, J = 6.9 Hz, 2H), 3.82 (s, 3H), 6.76-7.12 (m, 4H). LC-MS (METCR1410): 100% (UV), Rt= 0.70 min, m/z (ESI⁺)= 196.1 [M+H]⁺

References:

WO2018/50631,2018,A1 Location in patent:Paragraph 0439