Triethylamine → 1-{4'-[4-(3-Hydroxy-propyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

Temperatur

0 °C

1-{4′-[4-(2-Carboxy-ethyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester (0.336 g, 0.8 mmol) and triethylamine (0.145 mL, 1.04 mmol) were dissolved in THF (6.6 mL) under N2 atmosphere and cooled to 0° C. Isobutyl chloroformate (0.126 mL, 0.96 mmol) was added and the reaction stirred for 40 minutes and was then filtered, rinsing with dioxane and THF, and the filtrate was collected and concentrated. The crude material was dissolved in THF (10 mL), H2O (4.4 mL), and EtOH (1.9 mL), and then sodium borohydride (0.176 g, 4.6 mmol) was added. The reaction was heated to 50° C. for five hours then cooled and submitted to standard aqueous workup. The residue was purified on silica gel (0-80% EtOAc in hexanes) to yield the title compound.

1. filtrationwas then filtered
2. washrinsing with dioxane and THF
3. customthe filtrate was collected
4. concentrationconcentrated
5. dissolutionThe crude material was dissolved in THF (10 mL)
6. temperatureThe reaction was heated to 50° C. for five hours
7. temperaturethen cooled
8. customThe residue was purified on silica gel (0-80% EtOAc in hexanes)

ORD-Eintrag

ord-8a73b1141d844adbaf68a481f8c1a2a4

Quelldatensatz

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08217066B2