(E)-4-(((S)-1-((1r,3R,5R,7S)-3-Hydroxyadamantan-1-yl)-2-((1S,3R,5S)-3-isocyano-2-azabicyclo[3.1.0]hexan-2-yl)-2-oxoethyl)amino)-4-oxobut-2-enoic Acid

Ref. TR-H750115

Product Information

• Name: (E)-4-(((S)-1-((1r,3R,5R,7S)-3-Hydroxyadamantan-1-yl)-2-((1S,3R,5S)-3-isocyano-2-azabicyclo[3.1.0]hexan-2-yl)-2-oxoethyl)amino)-4-oxobut-2-enoic Acid
• Synonyms: (E)-4-[[(1S)-1-[(5S,7R)-3-hydroxy-1-adamantyl]-2-[(1S,3R,5S)-3-isocyano-2-azabicyclo[3.1.0]hexan-2-yl]-2-oxoethyl]amino]-4-oxobut-2-enoic acid

Description

Applications (E)-4-(((S)-1-((1r,3R,5R,7S)-3-Hydroxyadamantan-1-yl)-2-((1S,3R,5S)-3-isocyano-2-azabicyclo[3.1.0]hexan-2-yl)-2-oxoethyl)amino)-4-oxobut-2-enoic Acid is an impurity of Saxagliptin (S143500). Saxagliptin is a potent and selective reversible inhibitor of dipeptidyl peptidase-4, which is being developed for the treatment of type 2 diabetes.
References Feng, J., et al.: J. Med. Chem., 50, 2297 (2007); Rosenstock, J., et al.: Diabetes Obes. Metab., 10, 376 (2008); Thomas, L., et al.: J. Pharmacol. Exp. Ther., 325, 175 (2008);

• Brand: TRC

Chemical properties

• Molecular weight: 413.467
• Formula: C₂₂H₂₇N₃O₅
• Color/Form: Neat
• InChI: InChI=1S/C22H27N3O5/c1-23-16-6-14-5-15(14)25(16)20(29)19(24-17(26)2-3-18(27)28)21-7-12-4-13(8-21)10-22(30,9-12)11-21/h2-3,12-16,19,30H,4-11H2,(H,24,26)(H,27,28)/b3-2+/t12-,13+,14-,15-,16-,19+,21+,22-/m0/s1
• SMILES: [C-]#[N+][C@@H]1C[C@@H]2C[C@@H]2N1C(=O)[C@@H](NC(=O)/C=C/C(=O)O)[C@@]12C[C@@H]3C[C@@H](C[C@@](O)(C3)C1)C2