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

온도

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 기록

ord-672268a5a53c4628aab83eac7a551d0a

출처 데이터셋

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09090573B2