Reaktion #1802252

Reaktionsgleichung

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

→

ester

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

Lösungsmittel

EtOAc

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe reaction was charged with H2
2. 2
   Sonstigedegassed
3. 3
   workup.ADDITIONrefilled with hydrogen three times
4. 4
   Filtrationfiltered through a plug of Celite, and solvent
5. 5
   Sonstigewas removed under reduced pressure

Vorschrift

To a stirring solution of (7S)-7-benzyloxycarbonylamino-7-(quinolin-6-ylcarbamoyl)-heptanoic acid tert-butyl ester (11.0 g, 21.8 mmol) in EtOAc and MeOH was added 10% Pd/C. The reaction was charged with H2, degassed and refilled with hydrogen three times. The slurry was stirred at RT for 2 h at balloon pressure, then filtered through a plug of Celite, and solvent was removed under reduced pressure. The hydrogenolysis of the ester yielded 8.0 g (99%) of a thick oil solid after 19 h. 1H NMR (CDCl3) δ 8.9-7.3 (7H, m), 3.96 (1H, m), 2.31 (2H, t), 2.0-1.2 (17H, m). MS (ESI): (MH+) 372.2.

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