3-(2H-1,2,3,4-Tetrazol-5-yl)propanoic Acid synthesis

Yield:-

Reaction Conditions:

Stage #1:methyl 3-[2H-1,2,3,4-tetrazol-5-yl]propanoate with water;sodium hydroxide in methanol at 20; for 2 h;
Stage #2: with hydrogenchloride in water

Steps:

4.2
To a stirred solution of 3-(2H-tetrazol-5-yl)-propionic acid methyl ester (leq) in MeOH (15vol) was added NaOH (2eq) dissolved in water (2vol). The reaction mixture was stirred at rt for 2 hrs. A further 2eq of NaOH was added and the reaction stirred for an additional 2 hrs. The reaction mixture was concentrated in vacuo and the resultant solids dissolved in water (4vol), acidified with concentrated HCl and extracted with DCM (2 x 60vol). The combined organic layers were dried over MgSO₄, filtered and solvent removed in vacuo to give 3-(2H-tetrazol-5-yl)- propionic acid as a brown solid.

References:

CHDI, INC.;WITYAK, John;TOLEDO-SHERMAN, Leticia, M.;LEEDS, Janet;DOMINGUEZ, Celia;COURTNEY, Stephen, M.;YARNOLD, Christopher, J.;DE AGUIAR PENA, Paula, C.;SCHEEL, Andreas;WINKLER, Dirk WO2010/11302, 2010, A1 Location in patent:Page/Page column 54