Tetramethyltin → N-Isoamyl-N-(6-methyl naphthalene-2-sulfonyl)-D-valine tert-butyl ester

Temperatur

80 °C

To a solution of N-isoamyl-N-(6-trifluoromethanesulfonyloxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester (1.1 g, 1.89 mmol) in N,N-dimethylformamide (20 mL) is added lithium chloride (0.40 g, 9.5 mmol), tetramethyl tin (0.525 mL, 3.79 mmol), and bistriphenylphosphino palladium dichloride (0.066 g, 0.095 mmol). The reaction is heated to 80° C. for 16 h. The reaction is allowed to cool to ambient temperature and filtered through Celite. The filtrate is poured over water and extracted three times with dichloromethane. The combined organic extracts were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue is purified by column chromatography (4% hexanes-ethyl acetate) to afford the title compound as a white solid (0.41 g, 50% yield).

1. temperatureto cool to ambient temperature
2. filtrationfiltered through Celite
3. additionThe filtrate is poured over water
4. extractionextracted three times with dichloromethane
5. washThe combined organic extracts were washed with brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated in vacuo
8. customThe residue is purified by column chromatography (4% hexanes-ethyl acetate)

ORD-Eintrag

ord-457daebb59124a8c80dea501b501c76d

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08841291B2