The crystal structure and absolute configuration of the two new title nelfinavir analogs, C24H35ClN4O5, (I), and C27H39ClN4O5, (II), have been determined. Each of these molecules exhibits a number of disordered moieties. There are intramolecular N—H...O hydrogen bonds in both (I) and (II). In (I) it involves the two carboxamide groups, while in (II) it involves the N-tert-butyl carboxamide group and the 2-hydroxyl O atom. The intermolecular hydrogen bonding in (I) (O—H...O and N—H...O) leads to two-dimensional sheets that extend parallel to the ac plane. The intermolecular hydrogen bonding in (II) (O—H...O) leads to chains that extend parallel to the a axis.