Reacción #1010580

Ecuación de reacción

(R)-2-amino-2-phenylacetic acid

1-bromo-2-(2-bromoethoxy)ethane

sodium carbonate

→

title compound

(R)-2-morpholino-2-phenylacetic acid

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling
2. 2
   Otrothe resultant solid was removed by filtration
3. 3
   Lavadowashed with ethanol
4. 4
   ConcentraciónThe filtrate was concentrated
5. 5
   workup.DISSOLUTIONdissolved in ethanol
6. 6
   workup.ADDITIONa solution of 4N aqueous hydrochloric acid added until the pH of the solution
7. 7
   OtroThe resultant solid was removed
8. 8
   ConcentraciónThe filtrate was concentrated
9. 9
   Otropurified by reversed phase chromatography (C18)
10. 10
    Lavadoeluting with 10-100% acetonitrile in water (0.1% TFA)

Procedimiento

To (R)-2-amino-2-phenylacetic acid (1.0 g, 6.62 mmol), 1-bromo-2-(2-bromoethoxy)ethane (1.686 g, 0.727 mmol) and sodium carbonate (2.103 g, 19.85 mmol) was added ethanol (40 mL) and the resultant mixture heated at 100° C. for 45 hours. After cooling, the resultant solid was removed by filtration and washed with ethanol. The filtrate was concentrated, and then dissolved in ethanol then a solution of 4N aqueous hydrochloric acid added until the pH of the solution was 3. The resultant solid was removed and discarded. The filtrate was concentrated and purified by reversed phase chromatography (C18), eluting with 10-100% acetonitrile in water (0.1% TFA) to give the title compound. MS (ESI) m/z 222 (MA)+.

Fuente