PubMed · 14076503
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J SWIDINSKY, J KERVENSKI, B B BROWN. 1963. CATECHOL MONOGLYCERYL ETHER CARBAMATES.. https://doi.org/10.1002/jps.2600521009
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1-Benzyl-3-cyanopyrrole-2-carbonyl azide (5) underwent a Curtius rearrangement followed by quenching with alcohols to form the corresponding carbamates (6a-c). The carbamates 6a,b were unblocked to give the desired 2-amino-1-benzyl-3-cyanopyrrole (1a). A more facile procedure was subsequently developed for the synthesis of 1-substituted 2-amino-3-cyanopyrroles. N-Substituted aminoacetaldehyde dimethyl acetals (7a-c) were condensed with malononitrile in the presence of p-toluenesulfonic acid monohydrate to afford the corresponding 1-substituted 2-amino-3-cyanopyrroles (1a-c).
Covalent immobilization of 3,5-dimethylphenylcarbamate derivative of cellulose was performed in situ onto native silica monoliths cladded in a 50 mm x 4.6 mm polyether ether ketone high-performance liquid chromatographic (HPLC) column. The covalent attachment of cellulose derivative in the range of 16-19% (w/w) was performed via an epoxide moiety. The column obtained by this technique combines the high enantiomer-resolving ability of the polysaccharide derivative with favourable dynamic properties of monolithic HPLC columns. The covalent attachment of the cellulose derivative enables this column to be used in combination with the mobile phases which are incompatible with coated-type polysaccharide columns due to solubility of chiral selector in some organic solvents.
Efficient and industrially applicable synthetic processes for precursors of HIV protease inhibitors (Amprenavir, Fosamprenavir) are described. These involve a novel and economical method for the preparation of a key intermediate, (3S)-hydroxytetrahydrofuran, from l-malic acid. Three new approaches to the assembly of Amprenavir are also discussed. Of these, a synthetic route in which an (S)-tetrahydrofuranyloxy carbonyl is attached to l-phenylalanine appears to be the most promising manufacturing process, in that it offers satisfactory stereoselectivity in fewer steps.