Process of making 3-(4′-aminophenyl)-2-methoxypropionic acid, and analogs and intermediates thereof

A process for preparing a substantially optically pure compound of Formula (VII):

• the process comprising:
• reacting a compound of Formula (I):
• with an activating agent, in the presence of an amine base, to form an intermediate of Formula (I-A):
• wherein LG is a leaving group;
• treating the intermediate of Formula (I-A) with a base solution in the presence of an alcohol solvent, to eliminate the leaving group and thereby forming an intermediate of Formula (I-B):
• hydrolyzing the intermediate of Formula (I-B) to form a compound of Formula (IV):
• hydrogenating the compound of Formula (IV) to form a compound of Formula (V):
• resolving the compound of Formula (V) to form a substantially optically pure compound of Formula (VI):
• and
• acylating the compound of Formula (VI) to form the compound of Formula (VII), wherein the substantially optically pure compound of Formula (VII) is at least 95% of the enantiomer:
• expressed as a percentage of both enantiomers.