Reaction #7179

Reaction equation

4-[2-(tert-Butoxycarbonylamino)ethoxy]-3-methoxy-N-[3-[(E)-2-(3-methylphenyl)vinyl]phenyl]phenylacetamide

→

4-[2-(tert-butoxycarbonylamino)ethoxy]-3-methoxy-N-[3-[2-(3-methylphenyl)ethyl]phenyl]phenylacetamide

Yield 79.7%

Solvents

methanol

acetic acid

Conditions

Workup

1. 1
   Otheris subjected to catalytic hydrogenation at 50° C
2. 2
   OtherThe catalyst is removed by filtration
3. 3
   Otherthe solvent is evaporated

Procedure

4-[2-(tert-Butoxycarbonylamino)ethoxy]-3-methoxy-N-[3-[(E)-2-(3-methylphenyl)vinyl]phenyl]phenylacetamide (100 mg) is dissolved in methanol (10 ml) and acetic acid (1 ml), and thereto is added 10% palladium on carbon (10 mg), and the mixture is subjected to catalytic hydrogenation at 50° C. The catalyst is removed by filtration, and the solvent is evaporated to give 4-[2-(tert-butoxycarbonylamino)ethoxy]-3-methoxy-N-[3-[2-(3-methylphenyl)ethyl]phenyl]phenylacetamide (80 mg). This product is treated with 10% hydrogen chloride-methanol to give the desired compound (50 mg).

Source