Reaktion #1802253

Reaktionsgleichung

(7S)-7-amino-7-(quinolin-6-ylcarbamoyl)-heptanoic acid tert-butyl ester

benzoyl chloride

triethylamine

→

product

Ausbeute 78.9%

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

Ausbeute 78.9%

Lösungsmittel

MeCN

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITat RT for 2 h
2. 2
   SonstigeThe solvent was removed
3. 3
   workup.DISSOLUTIONresidue was dissolved in 400 mL EtOAc
4. 4
   workup.STIRRINGstirred with 100 mL 0.5 M NaHCO3 for 1 h
5. 5
   SonstigeThe aqueous layer was removed
6. 6
   Waschenthe organic layer was washed with 100 mL 0.5 M NaHCO3
7. 7
   TrocknenThe solution was dried over anhydrous Na2SO4

Vorschrift

To a stirring solution of (7S)-7-amino-7-(quinolin-6-ylcarbamoyl)-heptanoic acid tert-butyl ester (8.0 g, 21.6 mmol) in dry MeCN (100 mL) and to this solution was added benzoyl chloride (2.78 mL, 23.8 mmol) and triethylamine (6.1 mL, 43.2 mmol). The solution was stirred at 0° C. for 1 h, then at RT for 2 h. The solvent was removed, and residue was dissolved in 400 mL EtOAc, and stirred with 100 mL 0.5 M NaHCO3 for 1 h. The aqueous layer was removed, and the organic layer was washed with 100 mL 0.5 M NaHCO3, then with 50 mL water. The solution was dried over anhydrous Na2SO4. The product (8.1 g) was obtained after column purification (EtOAc as eluent) in 78.8% yield as a thick oil. 1H NMR (CDCl3) δ 9.40 (1H, s), 8.80 (1H, d), 8.22 (1H, d), 8.0-7.0 (10H, m), 5.0 (1H, m), 2.2-1.2 (19H, m). MS (ESI): (MH+) 476.1.

Quelle