Reaktion #2496115

Reaktionsgleichung

HATU

1-Methyl-1H-pyrazol-3-amine

DIEA

2-(1-(tert-butoxycarbonylamino)cyclobutyl)-2-hydroxyacetic acid

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title product

Ausbeute 92.3%

tert-butyl 1-(1-hydroxy-2-(1-methyl-1H-pyrazol-3-ylamino)-2-oxoethyl)-cyclobutylcarbamate

Ausbeute 92.3%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigeno starting material and the solvent was removed by rotary evaporation
3. 3
   workup.DISSOLUTIONThe crude product was dissolved in 40 mL EtOAc
4. 4
   Waschenwashed with 25 mL sat. NaHCO3(aq)
5. 5
   TrocknenThe organic phase was dried with Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated to dryness
8. 8
   SonstigeThe crude product was purified on a 25 g silica column on a Biotage Flashmaster, which

Vorschrift

1-Methyl-1H-pyrazol-3-amine (158 mg, 1.63 mmol) and DIEA (1.08 mL, 6.52 mmol) was added to a solution of 2-(1-(tert-butoxycarbonylamino)cyclobutyl)-2-hydroxyacetic acid (400 mg, 1.63 mmol) dissolved in DMF (20 mL). The solution was cooled to 0° C. and after 10 minutes HATU (620 mg, 1.63 mmol) was added. After approximately 2 hours at RT, LC-MS showed product and no starting material and the solvent was removed by rotary evaporation. The crude product was dissolved in 40 mL EtOAc and washed with 25 mL sat. NaHCO3(aq). The organic phase was dried with Na2SO4, filtered and evaporated to dryness. The crude product was purified on a 25 g silica column on a Biotage Flashmaster, which gave the title product as a white solid (488 mg, 92%). TLC rf: 0.07 in heptane:ethyl acetate 1:1. [M+H]+=325.

Quelle