Reaktion #622518

Reaktionsgleichung

1-tert-butoxycarbonylamino-cyclobutanecarboxylic acid

N,O-dimethylhydroxylamine

HCl

DIEA

HATU

→

product

Ausbeute 87.0%

2-(1-((tert-butoxycarbonyl)amino)cyclobutyl)-2-hydroxyacetic acid

Ausbeute 87.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the solution (which turned yellow on addition)
2. 2
   SonstigeAfter 2 hrs the DMF was removed by rotary evaporation at reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in EtOAc (100 mL)
4. 4
   Waschenwashed twice with 10% citric acid (aq) and saturated NaHCO3(aq) solution
5. 5
   TrocknenThe organic phase was dried with Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated on silica
8. 8
   SonstigeThe product was purified by flash chromatography (heptane: ethyl acetate (1:1)

Vorschrift

To a solution of 1-tert-butoxycarbonylamino-cyclobutanecarboxylic acid (3 g, 13.94 mmol) in dry DMF (50 mL) was added N,O-dimethylhydroxylamine×HCl (1.36 g, 13.94 mmol) and DIEA (9.21 mL, 55.75 mmol). The reaction flask was cooled to 0° C. and after 10 minutes HATU (5.30 g, 13.94 mmol) was added to the solution (which turned yellow on addition). After 2 hrs the DMF was removed by rotary evaporation at reduced pressure. The residue was dissolved in EtOAc (100 mL) and washed twice with 10% citric acid (aq) and saturated NaHCO3(aq) solution. The organic phase was dried with Na2SO4, filtered and evaporated on silica. The product was purified by flash chromatography (heptane: ethyl acetate (1:1) to give the product as a colourless oil that slowly crystallizes (3.13 g) in 87% yield.

Quelle