Réaction #1010580

Équation de réaction

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

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

sodium carbonate

→

title compound

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

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling
2. 2
   Autrethe resultant solid was removed by filtration
3. 3
   Lavagewashed with ethanol
4. 4
   ConcentrationThe 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
   AutreThe resultant solid was removed
8. 8
   ConcentrationThe filtrate was concentrated
9. 9
   Autrepurified by reversed phase chromatography (C18)
10. 10
    Lavageeluting with 10-100% acetonitrile in water (0.1% TFA)

Mode opératoire

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)+.

Source