Reaktion #1356010

Reaktionsgleichung

ethyl acetate

(7S)-7-Benzyloxycarbonylamino-octanedioic acid 8-tert-butyl ester

6-aminoquinoline

EDCI

→

compound

(7S)-7-BENZYLOXYCARBONYLAMINO-7-(QUINOLIN-6-YLCARBAMOYL)-HEPTANOIC ACID TERT-BUTYL ESTER

Lösungsmittel

CH3CN

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue was dissolved in 500 mL EtOAc
3. 3
   Waschenwashed with 1 M HCl (200×3) and water (100×2)
4. 4
   TrocknenThe organic layer was dried over anhydrous Na2SO4 Removal of solvent
5. 5
   Sonstigegave 16 g crude product

Vorschrift

(7S)-7-Benzyloxycarbonylamino-octanedioic acid 8-tert-butyl ester (10.0 g, 26.3 mmol), 6-aminoquinoline (4.02 g, 27.9 mmol) and EDCI (6.07 g, 29.0 mmol) were dissolved in 150 mL anhydrous CH3CN. The solution was stirred at RT for 2 h. The solvent was removed under reduced pressure, and the residue was dissolved in 500 mL EtOAc and washed with 1 M HCl (200×3) and water (100×2). The organic layer was dried over anhydrous Na2SO4 Removal of solvent gave 16 g crude product. The pure compound 9.0 g was obtained with column separation (ethyl acetate as eluent) in 68% as a thick oil. 1H NMR (CDCl3) δ 8.80 (1H, d), 8.70 (1H, s), 8.30 (1H, d), 8.00 (2H, t), 7.56–7.20 (7H), 5.40 (1H, d), 5.08 (2H, s), 4.38 (1H, m), 2.20 (2H, t), 2.0–1.6 (17H, m). MS (ESI): (MH+) 506.3.

Quelle