Patent ID: 7365188

Claim:
A process for producing a N 4 -acyl-5′-deoxy-5-fluorocytidine compound of formula: wherein R 2 is alkyl, cycloalkyl, aralkyl, aryl, or alkoxy, said process comprising: (a) admixing 5-fluorocytosine of formula: with a first silylating agent in the presence of an organic acid catalyst to produce a first silylated compound; (b) admixing the first silylated compound with a 2,3-diprotected-5-deoxy furanoside of formula: to produce a coupled product, wherein Y is a leaving group; and R 3 is a hydroxy protecting group; (c) admixing the coupled product with a second silylating agent to produce a second silylated compound, wherein the second silylating agent may be the same as or different from the first silylating agent; (d) acylating the second silylated compound with an acylating agent of formula: X—C(═O)—R 2 to produce an acylated product, wherein X is introduced as an acyl activating moiety by reaction with a reagent selected from the group consisting of: anhydrides, acyl halides, and thioesters; and R 2 is alkyl, cycloalkyl, aralkyl, aryl, or alkoxy; and (e) adding at least one base to the acylated product to selectively remove a covalently linked silyl moiety and the hydroxy protecting groups, R 3 , to produce the N 4 -acyl-5′-deoxy-5-fluorocytidine compound of Formula I.