Reacción #1951017

Ecuación de reacción

p-propargyloxyphenylalanine

1

2-Amino-3-phenylpropionic acid

HCl

2-Amino-3-phenylpropionic acid

Water

→

2-Amino-3-[4-(prop-2-ynyloxy)phenyl]-propionic acid propargyl ester

Disolventes

NaOH

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITthe mixture was kept at 4° C. overnight
2. 2
   FiltraciónThe precipitate was filtered
3. 3
   Lavadowashed with ice-cold H2O
4. 4
   Otrodried under vacuum
5. 5
   Otroyielding

Procedimiento

The propargyl ester (1.6 g, 5.5 mmol) from the previous step was dissolved in a mixture of aqueous 2 N NaOH (14 mL) and MeOH (10 mL). After stirring for 1.5 h at room temperature, the pH was adjusted to 7 by adding conc. HCl. Water (20 mL) was added and the mixture was kept at 4° C. overnight. The precipitate was filtered, washed with ice-cold H2O, and dried under vacuum yielding, 1.23 g (90%) of 1 in FIG. 11 (2-Amino-3-phenylpropionic acid (1) (also known as p-propargyloxyphenylalanine) as a white solid. 1H NMR (400 MHz, D2O) (as the potassium salt in D2O) δ 7.20 (d, J=8.8 Hz, 2H), 6.99 (d, J=8.8 Hz, 2H), 4.75 (s, 2H), 3.50 (dd, J=5.6, 7.2 Hz, 1H), 2.95 (dd, J=5.6, 13.6 Hz, 1H), 2.82 (dd, J=7.2, 13.6 Hz, 1H); 13C NMR (100 MHz, D2O) δ 181.3, 164.9, 155.6, 131.4, 130.7, 115.3, 57.3, 56.1, 39.3, HRMS (CI) m/z 220.0969 [C12H13NO3 (M+1) requires 220.0968].

Fuente