The key precursor for the synthesis of novel influenza neuraminidase inhibitors, cis-4-azido-L-proline methyl ester hydrochloride (C6H11ClN4O2, Mr = 206.63), was prepared as white needle-shaped crystals and its structure was elucidated by single-crystal X-ray diffraction. In the crystal structure, molecules are linked through intermolecular hydrogen bonds, forming layers perpendicular to the bc plane.
AbrahamD.J., MokotoffM., ShehL., and SimmonsJ. E., J. Med. Chem., 1983, 26, 549.
14.
KleinL.L., LiL., ChenH. J., CurtyC. B., DeGoeyD. A., GrampovnikD. J., LeoneC. L., ThomasS. A., YeungC. M., FunkK. W., KishoreV., LundellE. O., WodkaD., MeulbroekJ. A., AlderJ. D., NiliusA. M., LarteyeP. A., and PlattnerJ. J., Total Bioorg. Med. Chem., 2000, 8, 1677.
15.
BaerT., MartinT., StadlwieserJ., WollinS. L., ZechK., SommerhoffC. P., and UlrichW. R., PCT Int. Appl, WO 2002060895, 2002.
16.
BaerT., StadlwieserJ., WollinS. L., ZechK., SommerhoffC. P., MartinT., and UlrichW. R., PCT Int. Appl, WO 2002102771, 2002.
17.
MartinT., and UlrichW. R., PCT Int. Appl, WO 2004012731, 2004.
18.
SonntagL.S., IvanS., LangerM., ConzaM. M., and WennemersH., Synlett, 2004, 7, 1270.
19.
SirionU., KimH. J., LeeJ. H., SeoJ. W., LeeB. S., LeeS. J., OhS. J., and ChiD. Y., Tetrahedron Lett, 2007, 48, 3953.
20.
HanB., KnustH., NettekovenM., RatniH., and WuX., PCT Int. Appl., WO 2008148689, 2008.
21.
MckillopA., TaylorR. J. K., WatsonR. J., and LewisN., Synthesis, 1994, 31.
22.
JordisU., SauterF., and SiddiqiS. M., Indian J. Chem. Sec. B, 1989, 28B, 294.
