[1-(5-MERCAPTO-[1,3,4]OXADIAZOL-2-YL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER synthesis

Yield:-

Reaction Conditions:

with 4-methyl-morpholine in ethanol; for 0.333333 h;Sonication;

Steps:

General procedure: Z/Boc-protected-S-linked-1,3,4-oxadiazole tethered mimetics (5 and 8).

General procedure: To a solution of hydrazide 1 (10 mmol) in ethanol (10 mL) were added CS₂ (0.7 mL, 12 mmol) and NMM (1.3 mL, 12 mmol) and subjected to ultrasonication. After complete consumption of starting material (TLC, 20 min) NMM was added (1.3 mL, 12 mmol) followed by halogen derivative (12 mmol) and sonication was continued for another 20 min. The solvent was removed in vacuo and the resulting crude product was subjected to column chromatography (20% EtOAc in n-hexane) to obtain the analytically pure product.

References:

Sureshbabu, Vommina V.;Vasantha;Nagendra [Tetrahedron Letters,2012,vol. 53,# 11,p. 1332 - 1336] Location in patent:experimental part