Reaktion #326955

Reaktionsgleichung

D-Phenylglycine amide

1,3-propanesultone

→

title compound

Ausbeute 38.9%

3-{[(1S)-2-amino-2-oxo-1-phenylethyl]amino}-1-propanesulfonic acid

Ausbeute 38.9%

Lösungsmittel

tetrahydrofuran

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 2 hours
2. 2
   FiltrationThe solid was collected by filtration
3. 3
   Waschenwashed with acetone (2×20 mL)
4. 4
   workup.DISSOLUTIONThe solid was dissolved in 50% water/EtOH mL)
5. 5
   workup.ADDITIONDowex Marathon C ion exchange resin (strongly acidic) was added to the solution
6. 6
   workup.STIRRINGThe suspension was stirred for 15 minutes before the resin
7. 7
   Sonstigewas removed by filtration
8. 8
   SonstigeThe filtrate was evaporated under reduced pressure
9. 9
   Filtrationfiltered
10. 10
    Sonstigedried in the vacuum oven (50° C.)

Vorschrift

To a solution of D-Phenylglycine amide (850 mg, 7.5 mmol) in tetrahydrofuran (10 mL) and 1,4-dioxane (4 mL) was added 1,3-propanesultone (818 mg, 6.8 mmol). The solution stirred at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration and washed with acetone (2×20 mL). The solid was dissolved in 50% water/EtOH mL). Dowex Marathon C ion exchange resin (strongly acidic) was added to the solution. The suspension was stirred for 15 minutes before the resin was removed by filtration. The filtrate was evaporated under reduced pressure. The solid was suspended in acetone (50 mL), filtered and dried in the vacuum oven (50° C.), affording the title compound (720 mg, 34%). 1H NMR (D2O, 500 MHz) δ ppm 7.38 (m, 5H), 4.92, (s, 1H), 3.00 (m, 1H), 2.90 (m, 1H), 2.78 (m, 2H), 1.97 (m, 2H). 13C (D2O, 125 MHz) δ ppm 170.14, 130.95, 130.24, 129.94, 128.74, 63.40, 47.99, 44.92, 21.27. [α]D=+106° (c=0.0016 in water), ES-MS 273 (M+1).

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