2-[(Acetylthio)methyl]-3-phenylpropionic Acid → N-(3-Acetylthio-2-benzylpropionyl)-O-benzyl-L-tyrosine Methyl Ester

Participants

Reaction Steps

React O-benzyl-L-tyrosine methyl ester hydrochloride (2.77 g) and 3-acetylthio-2-benzylpropionic acid (2.05 g) in a manner similar to that described in Example 1, Step 1 to give a yellow-orange oil. Chromatograph this oil on a column of silica gel (2.5 L) and elute with CH2Cl2 :ethyl acetate 98:2 to give Isomer A, a white solid (0.84 g) m.p. 108°-109°; [α]D26 =-39.8° (MeOH); overlap Isomer A and Isomer B (0.80 g); and Isomer B, white solid (0.45 g), m.p. 92-93°, [α]D26 =+19.2° (MeOH).

Provenance & Evidence