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An efficient synthesis of a 4'-phosphonodifluoromethyl-3'-formyl-phenylalanine containing SRC SH2 ligand

W C Shakespeare1, R S Bohacek, S S Narula

  • 1ARIAD Pharmaceuticals, Inc., Cambridge, MA 02139-4234, USA.

Bioorganic & Medicinal Chemistry Letters
|November 24, 1999
PubMed

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...