An efficient synthesis of the angiotensin II inhibitor Valsartan (Diovan) is presented. The formation of the aryl–aryl bond represents the key step of its synthesis, which has been done by a Suzuki coupling of aryl boronate with 2-bromophenyl oxazoline with good yield and purity. This method overcomes many of the drawbacks associated with the previously reported syntheses.
WyvrattM.J., and PatchettA. A., Med. Res. Rev., 1985, 5, 483.
2.
DunciaJ.V., ChiuA. T., CariniD. J., GregoryG. B., JohnsonA. L., PriceW. A., WellsG. J., WongP. C., CalabreseJ. C., and TimmermansP.B. M. W. M., J. Med. Chem., 1990, 33, 1312.
CariniD.J., DunciaJ. J. V., AldrichP. E., ChiuA. T., JohnsonA. L., PierceM. E., PriceW. A., SantellaJ.B.III, WellsG. J., WexlerR. R., WongP. C., YooS., and TimmermansP.B. M. W. M., J. Med. Chem., 1991, 34, 2525.
5.
NegishiE., KingA. O., and OkukadoN., J. Org. Chem., 1977, 42, 1821.