title: An efficient process for the synthesis of cyclic HPMPC.
abstract: 1-[((S)-2-Hydroxy-2-oxo-1,4,2-dioxaphosphorinan-5-yl)methyl] cytosine (cyclic HPMPC) was readily synthesized in gram to multi-kilogram quantities by treating a DMF suspension of HPMPC with four molar equivalents of ethyl chloroformate. This dehydrative intramolecular cyclization process typically afforded cHPMPC in 94% isolated yield and high purity. Benign by-products and solvents were easily removed.
authors.affiliation: Gilead Sciences, 333 Lakeside Drive, Foster City, California 94403, USA.
authors.forename: M S
authors.initials: MS
authors.lastname: Louie
authors.forename: H
authors.initials: H
authors.lastname: Chapman
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis*; D000077404:Cidofovir; D003596:Cytosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D005563:Formic Acid Esters / Q000737:chemistry; D063065:Organophosphonates; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000998:Antiviral Agents; D005563:Formic Acid Esters; D063065:Organophosphonates; D009943:Organophosphorus Compounds; C007658:ethyl chloroformate; C072572:cyclic-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine; D003596:Cytosine; D000077404:Cidofovir