Reaktion #46761

Reaktionsgleichung

Mono-N-Boc-1,2-diaminoethane

1,4-dioxane

K2CO3

3-fluoro-4-nitrobenzoic acid

→

title compound

Ausbeute 84.0%

3-(2-tert-Butyoxycarbonylaminoethylamino)-4-nitrobenzoic acid methyl ester

Ausbeute 84.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 2 L flask equipped with a stir bar
2. 2
   EinengenThe reaction mixture was concentrated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2 (400 mL)
4. 4
   SonstigeThe heterogeneous mixture was transferred to a separatory funnel
5. 5
   Sonstigewhere the aqueous phase was separated
6. 6
   Extraktionre-extracted with CH2Cl2 (2×100 mL)
7. 7
   Waschenwashed with H2O (5×100 mL)
8. 8
   Trocknendried over Na2SO4
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated under reduced pressure

Vorschrift

A 2 L flask equipped with a stir bar was charged with 1,4-dioxane (300 mL), DMF (40 mL), K2CO3 (10 g) and 3-fluoro-4-nitrobenzoic acid (9.7 g). Mono-N-Boc-1,2-diaminoethane (8.6 g) was added to the reaction mixture and stirred for 12 h at 60° C. The reaction mixture was concentrated and the residue was dissolved in CH2Cl2 (400 mL) and H2O (500 mL). The heterogeneous mixture was transferred to a separatory funnel where the aqueous phase was separated and re-extracted with CH2Cl2 (2×100 mL). The organic phases were combined and washed with H2O (5×100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to provide the title compound as an orange solid (14 g, 84%).

Quelle