Hydrochloric Acid → (S)-1-((R)-5-(2,5-difluorophenyl)-2-((methoxy-methoxy)methyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-hydroxypropan-1-one

To a cooled (0° C.) solution of (S)-2-(tert-butyldiphenylsilyloxy)-1-((R)-5-(2,5-difluorophenyl)-2-((methoxymethoxy)methyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)propan-1-one (110 mg, 0.17 mmol) in THF (10 mL) was added TBAF (0.28 mL, 1.0 M, 0.28 mmol). After slowly warming to room temperature and stirring for 16 hours, the mixture was treated with 0.5 N HCl (30 mL) and extracted with ethyl acetate (2×30 mL). The combined organics were washed with NaHCO3 (30 mL) and brine (30 mL), dried over Na2SO4, and concentrated under reduced pressure. The pale yellow residue was chromatographed (9:1 to 4:1 hexanes/ethyl acetate) to provide the product as a white solid (0.045 g, 64%).

1. extractionextracted with ethyl acetate (2×30 mL)
2. washThe combined organics were washed with NaHCO3 (30 mL) and brine (30 mL)
3. dry with materialdried over Na2SO4
4. concentrationconcentrated under reduced pressure
5. customThe pale yellow residue was chromatographed (9:1 to 4:1 hexanes/ethyl acetate)

ORD-Eintrag

ord-966b65ae275949eabc0e8938ffb2a86f

Quelldatensatz

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08623895B2