2,3-Diphenylpropionic acids as potent VLA-4 antagonists

Substituent position-driven reaction pathways in the heterogeneous one-pot reduction/asymmetric hydrogenation of nitro-substituted (E)-2,3-diphenylpropenoic acids over Pd catalyst

“…Moreover, the amino acids resulted by the hydrogenation of acids substituted on the 3-phenyl ring in para position were obtained in good, up to 80 % enantioselectivities. Considering that these amino acids are useful intermediates in the preparation of various 2,3-diphenylpropionic acid derivatives of pharmaceutical importance, 13 the reported heterogeneous catalytic method deserves further attention.…”

Determination of Solvent‐Trapped Products Obtained by Photolysis of Aryl Azides in 2,2,2‐Trifluoroethanol

“…19 :34 A solution of HNO 3 (60 %; 480.0 mg, 7.60 mmol) in acetic acid (5.0 mL) was added dropwise to a stirred solution of 4‐methoxyphenylacetic acid ethyl ester ( 14 ) (1.25 g, 6.44 mmol) in acetic anhydride (10.0 mL) at 0 °C. The resulting reaction mixture was stirred at 0 °C for 1.5 h before being diluted with EtOAc (10 mL) and poured into ice water.…”

“…24 :34 The hydrogenation of 19 was conducted as described in the general procedure save for the use of EtOH/water 9:1 as solvent to give ethyl (3‐amino‐4‐methoxyphenyl)acetate ( 24 ) in 86 % yield as a light‐yellow oil. IR (neat); $\tilde \nu $ max =3458, 3370, 2922, 2853, 1726, 1611, 1517, 1448, 1223, 1143, 1030 cm −1 ; 1 H NMR (CDCl 3 , 600 MHz): δ =6.72 (d, J =8.1 Hz, 1 H), 6.65 (d, J =2.0 Hz, 1 H), 6.62 (dd, J =2.0 and 8.1 Hz, 1 H), 4.79 (br s, 2 H), 4.13 (q, J =7.1 H, 2 H), 3.83 (s, 3 H), 3.47 (s, 2 H), 1.25 ppm (t, J =7.1 Hz, 3 H); 13 C NMR (CDCl 3 , 151 MHz): δ =172.0, 146.4, 136.1, 126.7, 119.0, 115.8, 110.3, 60.7, 55.5, 40.8, 14.2 ppm; MS (EI+): m / z (%): 209 [ M ] + (100), 194 (39), 136 (88), 121 (37); HRMS (EI+): m / z calcd for C 11 H 15 NO 3 : 209.1052 [ M ] + ; found: 209.1032.…”

Reaction Integration Using Electrogenerated Cationic Intermediates

“…To demonstrate the power of the method, we synthesized a key intermediate for the synthesis of VLA-4 antagonist (Scheme 10). 20 The electrochemical oxidation of 22, which was prepared from commercially available material 21 in one step, in the presence of pyridine and the subsequent treatment with piperidine gave 23 in 89% isolated yield. The benzene ring bearing a nitro group was not affected during the course of the transformation.…”