Reaction #2345

Reaction equation

compound

Methyl 2-t-butoxycarbonylamino-4-[4-[4-(4-pyridyl)-piperazin-1-yl]phenoxy]butyrat

→

title compound

Yield 74.1%

Methyl 2-amino-4-[4-[4-(4-pyridyl) piperazin-1-yl]-phenoxy]butyrate

Yield 74.1%

Solvents

TFA

Conditions

Workup

1. 1
   OtherThe solution was evaporated
2. 2
   workup.DISSOLUTIONthe residue dissolved in water (15 ml)
3. 3
   ExtractionThe mixture was extracted three times with dichloromethane
4. 4
   OtherEvaporation of the combined extracts

Procedure

The compound of Example 140 (0.96 g) in TFA (10 ml) was kept at room temperature for 2 hours. The solution was evaporated and the residue dissolved in water (15 ml) and the solution basified with sodium carbonate. The mixture was extracted three times with dichloromethane. Evaporation of the combined extracts gave the title compound (0.56 g); m.p. 125°-127° C.; NMR(d6DMSO) δ 8.2(2H,d), 6.92(6H,m), 4.0(2H,m), 3.64(3H,s), 3.46(4H,t), 3.15(4H,t), 2.04(2H,m), 1.84(1H, m); m/e 371(M+H)+. Calculated for C20H26N4 O3. 0.75 H2O: C, 62.5; H, 7.17; N, 14.6. Found: C, 62.8; H, 6.8; N, 14.3%.

Source