Reacción #11665

Ecuación de reacción

3-methylpentanoic acid

1,1′-carbonyldiimidazol

trifluoroacetic acid

NaHCO3

{2-[(5-aminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester

→

5-[(3-Methyl-pentanoylamino)-methyl]-thiophene-2-carboxylic acid (2-amino-phenyl)-amide

Rendimiento 59.4%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added carefully
2. 2
   Extracciónthe aqueous phase was extracted three times with ethyl acetate
3. 3
   SecadoThe combined organic phases were dried over Na2SO4
4. 4
   OtroThe solvent was evaporated

Procedimiento

To a solution of 33.43 mg (0.288 mmol) 3-methylpentanoic acid in 1 ml THF were added 46.67 mg (0.288 mmol) 1,1′-carbonyldiimidazol. After 1 h at rt 100 mg (0.288 mmol) {2-[(5-aminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester were added and the reaction mixture was stirred for 3 h at rt. 1.7 ml trifluoroacetic acid were added and after 2 h at rt sat. aqueous NaHCO3 was added carefully and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over Na2SO4. The solvent was evaporated and the residue was subjected to silica gel chromatography (ethyl acetate/heptane 6:4) to yield 59.3 mg (0.171 mmol) 5-[(3-Methyl-pentanoylamino)-methyl]-thiophene-2-carboxylic acid (2-amino-phenyl)-amide; exact MW [M+H] calc'd: 346.16; MW found [M+H]: 346.4.

Fuente