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With triethylamine; In diethyl ether; at -20℃; for 0.583333h;
Isobutyl chloroformate (1.21 g, 8.90 mmol) was added to a well-stirred solution of Intermediate 7 (2.09 g, 8.72 mmol) and triethylamine (890 mg, 8.72 mmol) in dry ether (15 ml) at - 20 0C over 5 min under a nitrogen atmosphere. The reaction mixture was stirred for another 30 min at the same temperature and then filtered to remove the precipitated triethylamine hydrochloride. To the filtrate containing the mixed anhydride was slowly added a solution of diazomethane in diethyl ether until the yellow colour persisted (ca. 20 ml). The reaction mixture was gradually allowed to warm to room temperature and left overnight at this temperature. Excess diazomethane was quenched with a few drops of glacial acetic acid and then with 10 % citric acid solution. The organic layer was separated and the aqueous layer was extracted with ether (2 x 100 ml). The combined organic extracts were washed with saturated NaHCO3 solution, brine and dried (Na2SO4). The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography (30 % ethyl acetate in petroleum ether) to afford 1.12 g of the desired compound as a pale yellow solid; IR (KBr) 3355, 3079, 2136, 1685, 1614, 1530 cm"1; 1H NMR (CDCl3) 1.44 (s, 9H), 1.60-1.93 (m, 5H), 2.04-2.14 (m, IH), 2.82 (brs, IH), 4.06 (brs, IH), 5.28 (brs, IH).
(1S,3R)-[3-(quinolin-2-ylcarbamoyl)-cyclopentyl]-carbamic acid tert-butyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With EDAC; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;
Example 192A (1S,3R)-[3-(quinolin-2-ylcarbamoyl)-cyclopentyl]-carbamic acid tert-butyl ester To a solution of Example 191A (91.6 mg, 0.4 mmol) in DMF (4 mL) was added 2-aminoquinoline (64 mg, 0.44 mmol), EDAC (93 mg, 0.48 mmol), HOBT (82 mg, 0.6 mmol), and diisopropylethylamine (0.35 mL, 2 mmol). The mixture was stirred at room temperature overnight, diluted with ethyl acetate, washed with water (2 times) and brine. The organic layer was dried (sodium sulfate), filtered, concentrated under reduced pressure and purified by flash chromatography with 3% methanol/dichloromethane to provide the titled compound. MS (ESI) m/z 356 (M+H)+.
Example 195A <strong>[261165-05-3](1S,3R)-3-tert-butoxycarbonylamino-cyclopentanecarboxylic acid</strong> methyl ester To a cold solution (0 C.) of Example 191A (458 mg, 2 mmol)in THF (2 mL)/MeOH (2 mL) was added TMSCHN2 (2 mL, 2N in hexane). The mixture was stirred at room temperature for 2 hours, concentrated under reduced pressure and purified by flash chromatography with 30% acetone/hexane to provide the titled compound. MS (ESI) m/z 244 (M+H)+.
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