AbstractThe Beckmann rearrangement of steroidal oximes is reported. Different methods of esterification of homo‐aza‐steroids with carboxylic derivatives ofN,N‐bis(2‐chloroethyl)aniline are reported.The lipophilic nature of the steroidal hormones is the reason for searching compounds containing as the biological platform the steroid molecule and as the active moiety the alkylating agent, such as nitrogen mustards linked to the steroid with a stable bond or with an easily cleaved ester or ether molecule and different other active species, hopefully to transport and deliver the alkylating agent to the specific target tissue. The concept to design hybrid compounds containing as the biological platform steroidal lactams and as the alkylating congener carboxylic derivatives ofN,N‐bis(2‐chloroethyl)aniline might form compounds with synergistic activity.The findings suggest that the conformation of the alkylating agent influences the anticancer activity, while the amide group of the lactam molecule is important for activity in L1210 leukemia.These hybrid compounds with a modified steroid as the biological platform furnish derivatives with advantages compared to the unmodified steroids with alkylating agents.Different methods of esterification of homo‐aza‐steroids with carboxylic derivatives ofN,N‐bis(2‐chloro‐ethyl