Preparation of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl) -p-nitrobenzenesulfonylamide hydrochloride and other derivatives of 2-hydroxy-1,3-diamines

A process for the preparation of a compound having the following general formula:

• said process comprising:
• combining a halomethyl alcohol (HMA) with an amine and an acid scavenger to form a reaction mixture, and heating said reaction mixture until the reaction is complete, thereby forming the compound of Formula I;
• wherein said HMA has the following general formula:
• wherein:
• R1 is an amino acid side chain or a functionalized amino acid side chain;
• R2 is a protecting group;
• R3 and R4 are independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and —NHP, wherein P is selected from the group consisting of H, alkyl, cycloalkyl, aryl and a protecting group, or R3 and R4 together form a cyclic structure selected from the group consisting of quinoline and isoquinoline;
• and
• X is a leaving group.