Reaktion #60331

Reaktionsgleichung

4-Amino-chroman-7-carbonitrile

3-(naphthalen-2-ylsulfonylamino)-3-phenyl-propionic acid

HOBt

DIEA

EDC

→

title compound

N-(7-cyano-chroman-4-yl)-3-(naphthalen-2-ylsulfonylamino)-3-phenyl-propionamide

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe reaction solution was washed
2. 2
   workup.ADDITIONwith dilute (˜5%) NaHCO3—H2O and H2O, and solution
3. 3
   Trocknenwas dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   Sonstigeto provide a residue which
7. 7
   Sonstigewas purified by column chromatography (silica gel, 25% hexane in EtOAc)
8. 8
   Sonstigeto provide

Vorschrift

4-Amino-chroman-7-carbonitrile (Step E) (50 mg, 0.28 mmol), 3-(naphthalen-2-ylsulfonylamino)-3-phenyl-propionic acid (100 mg, 0.28 mmol), HOBt (42 mg, 0.31 mmol), and DIEA (72 mg, 0.56 mmol) were dissolved in CH2Cl2 (10 mL). EDC (52 mg, 0.34 mmol) was added and the reaction was stirred at 22-25° C. overnight until completed. The reaction solution was washed with dilute (˜5%) NaHCO3—H2O and H2O, and solution was dried over MgSO4, filtered and concentrated in vacuo to provide a residue which was purified by column chromatography (silica gel, 25% hexane in EtOAc) to provide the title compound as a white solid mixture of diastereomers (ca. 3:2 by 1H NMR after flash column chromotography).

Quelle