Reaktion #159585

Reaktionsgleichung

1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

1-hydroxybenzotriazole hydrate

N,N-diisopropylethylamine

→

title compound ( D26 )

tert-butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was then concentrated to half volume in vacuo
2. 2
   workup.ADDITIONpoured into water (60 ml)
3. 3
   Extraktionextracted with ethylacetate (3×60 ml)
4. 4
   WaschenThe combined organic phases were washed with saturated aqueous NH4Cl (100 ml), saturated aqueous NaHCO3 (100 ml), water and brine (100 ml)
5. 5
   Trocknendried with Na2SO4 anhydrous (50 g)
6. 6
   Einengenconcentrated under reduced atmosphere
7. 7
   SonstigeCollected organics after solvent evaporation

Vorschrift

A mixture of 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (D25) (5 g, 24.85 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (14.39 g, 75.55 mmol), 1-hydroxybenzotriazole hydrate (0.38 g, 2.48 mmol) and N,N-diisopropylethylamine (34.6 ml, 198 mmol) in dimethylformamide (80 ml) was stirred overnight at room temperature. The reaction mixture was then concentrated to half volume in vacuo, poured into water (60 ml) and extracted with ethylacetate (3×60 ml). The combined organic phases were washed with saturated aqueous NH4Cl (100 ml), saturated aqueous NaHCO3 (100 ml), water and brine (100 ml), dried with Na2SO4 anhydrous (50 g) and concentrated under reduced atmosphere. Collected organics after solvent evaporation afforded the title compound (D26) (5.33 g)

Quelle