Water → Deoxycholic Acid Impurity 69

Temperatur

25 °C

Ethyl aluminum dichloride (14.2 mL, 25 mmol, 1.8M in toluene) was added to a solution of methyl acrylate (1.89 mL, 20 mmol) in DCM (60 mL) at 0° C. under inert atmosphere. The resulting solution was stirred for 15 min and then compound 1.6a (3 g, 8.7 mmol) was added. After stirring for an additional 20 min at 0° C., the temperature was raised to 25° C. and held there for a further 18 h. At this point the reaction was determined to be complete by TLC, then the mixture was poured into cold (0° C.) water (60 mL). The phases were separated and the aqueous layer was extracted with DCM (60 mL). The organic layers were combined and washed sequentially with water (50 mL) and saturated brine solution (100 mL). It was then dried over anhydrous Na2SO4 (5 g) and filtered. The filtrate was concentrated under vacuum, providing compound 1.7b (2.6 g, 70%).

1. stirringAfter stirring for an additional 20 min at 0° C.
2. waitheld there for a further 18 h
3. customThe phases were separated
4. extractionthe aqueous layer was extracted with DCM (60 mL)
5. washwashed sequentially with water (50 mL) and saturated brine solution (100 mL)
6. dry with materialIt was then dried over anhydrous Na2SO4 (5 g)
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under vacuum

ORD-Eintrag

ord-fd08f710f8da4dc2a3879bf12d2fb432

Quelldatensatz

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07902387B2