Thioglycolic Acid → Tert-butyl 3-{4-[({2',6'-dimethyl-4'-[2-(2-oxopyrrolidin-1-yl)ethoxy]biphenyl-3-yl}methyl)amino]-2-fluorophenyl}propanoate

To a solution of tert-butyl 3-(4-{({2′,6′-dimethyl-4′-[2-(2-oxopyrrolidin-1-yl)ethoxy]biphenyl-3-yl}methyl)[(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate (0.91 g, 1.23 mmol) and mercaptoacetic acid (0.26 mL, 3.68 mmol) in N,N-dimethylformamide (9 mL) was added lithium hydroxide monohydrate (0.31 g, 7.38 mmol) under stirring at room temperature, and the mixture was stirred at the same temperature for 4 hr. The reaction mixture was concentrated under reduced pressure, and to the residue was added brine. The mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate-=5/1-ethyl acetate) to give the title compound (0.51 g, yield 74%) as a colorless amorphous powder.

1. stirringthe mixture was stirred at the same temperature for 4 hr
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. additionto the residue was added brine
4. extractionThe mixture was extracted with ethyl acetate
5. dry with materialThe extract was dried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate-=5/1-ethyl acetate)

ORD-Eintrag

ord-553a023231b0467e8f9528eedb32e999

Quelldatensatz

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07786165B2