Triethylamine → (S)-tert-butyl 1-cyano-2-(4-isopropoxyphenyl)ethylcarbamate

Temperatur

0 °C

Trichloroacetic acid anhydride (120 mg, 0.39 mmol) was added slowly to a solution of (S)-tert-butyl 1-amino-3-(4-isopropoxyphenyl)-1-oxopropan-2-ylcarbamate (50 mg, 0.2 mmol) in methylene chloride (3 mL) and triethylamine (86 uL, 0.62 mmol) at 0° C. The reaction was stirred for 1 h. at 0° C. The reaction was quenched with saturated NaHCO3 and was extracted with ethyl acetate. The organic phase was washed with water, saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product, which was purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1) to obtain the (S)-tert-butyl 1-cyano-2-(4-isopropoxyphenyl)ethylcarbamate (40 mg, 80%) as clear oil. Analytical LCMS (M+Na)+: m/z=327.0.

1. customThe reaction was quenched with saturated NaHCO3
2. extractionwas extracted with ethyl acetate
3. washThe organic phase was washed with water, saturated brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customto give the crude product, which
8. customwas purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1)

ORD-Eintrag

ord-ded7723687b84368be83e778da5e538d

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08481732B2