Tenofovir alafenamide Impurity 3 is a structurally related synthetic byproduct arising from the alafenamide side-chain coupling in the production of tenofovir alafenamide. It retains the cyclopropyl-methylphosphonate core but lacks the terminal 5โ-isobutylamino group, featuring an unmodified 2โ-deoxy-5โ-O-(4-methylphenyl) phosphonate linkage. This impurity results from incomplete amidation during API synthesis, leaving a free primary amine at the alafenamide terminus. It serves as a critical HPLC reference standard for monitoring process purity in tenofovir alafenamide manufacturing.
On RequestC[C@H](CN1C=NC2=C(N=CN=C21)N)OCP(=O)(OC3=CC=CC=C3)OC4=CC=CC=C4
InChI=1S/C21H22N5O4P/c1-16(12-26-14-25-19-20(22)23-13-24-21(19)26)28-15-31(27,29-17-8-4-2-5-9-17)30-18-10-6-3-7-11-18/h2-11,13-14,16H,12,15H2,1H3,(H2,22,23,24)/t16-/m1/s1
XWTDSRIRFPGRAW-MRXNPFEDSA-N