Reacción #330141

Ecuación de reacción

N2-phenylpyridine-2,3-diamine

(S)-2-tertbutoxycarbonylamino-3-methylbutyric acid

HOAt

4-methylmorpholine

N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

→

[(S)-2-methyl-1-(2-phenylaminopyridin-3-ylcarbamoyl)propyl]carbamic acid tert-butyl ester

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was partitioned between DCM
2. 2
   LavadoThe organic layer was washed with brine
3. 3
   Secadodried (MgSO4)
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   Otrothe resulting residue purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane)

Procedimiento

A mixture of N2-phenylpyridine-2,3-diamine (556 mg, 3.0 mmol), (S)-2-tertbutoxycarbonylamino-3-methylbutyric acid (0.72 g, 3.3 mmol), HOAt (0.450 g, 3.3 mmol), 4-methylmorpholine (0.73 mL, 6.6 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.63 g, 3.3 mmol) in DCM (15 mL) was stirred at RT for 18 h. The reaction mixture was partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic layer was washed with brine, dried (MgSO4), concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane) to afford [(S)-2-methyl-1-(2-phenylaminopyridin-3-ylcarbamoyl)propyl]carbamic acid tert-butyl ester as a white solid (1.13 g, quantitative).

Fuente