Reacción #87074

Ecuación de reacción

2-morpholinoacetic acid

HATU

(S)-Benzyl 2-((S)-2-(tert-butoxycarbonylamino)pent-4-ynamido)-3-(4-methoxy phenyl)propanoate

TFA

N-Methylmorpholine

→

(S)-Benzyl 3-(4-methoxyphenyl)-2-((S)-2-(2-morpholinoacetamido)pent-4-ynamido)propanoate

Rendimiento 69.0%

Disolventes

dichloromethane

Water

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was removed
2. 2
   Extracciónthe resulting mixture was extracted with dichloromethane (20 mL×3)
3. 3
   Secadodried over anhydrous sodium sulfate
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=200:1 to 100:1)

Procedimiento

(S)-Benzyl 2-((S)-2-(tert-butoxycarbonylamino)pent-4-ynamido)-3-(4-methoxy phenyl)propanoate (1.1 g, 2.3 mmol) was dissolved in dichloromethane (10 mL) and treated with TFA (1.5 mL) for 1 h at ambient temperature. The solvent was removed and the residue was added to a solution of 2-morpholinoacetic acid (0.33 g, 2.3 mmol) and HATU (1.0 g, 2.6 mmol) in dichloromethane (20 mL). N-Methylmorpholine (0.63 mL, 5.7 mmol) was added at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 1 h. Water (20 mL) was added and the resulting mixture was extracted with dichloromethane (20 mL×3). The organic extracts were combined, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=200:1 to 100:1) to afford (S)-Benzyl 3-(4-methoxyphenyl)-2-((S)-2-(2-morpholinoacetamido)pent-4-ynamido)propanoate (0.8 g, 69% yield) as a colorless solid.

Fuente