Isopropylamine → HCID 178457874, compound

Participants

Reaction Steps

Isopropylamine (925 μL, 10.86 mmol) was added to a stirred solution of trans 4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (1.32 g, 5.43 mmol), HATU (2.06 g, 5.43 mmol) and diisopropylethylamine (2.79 mL, 16.3 mmol) in DMF (50 ml). The resulting mixture was stirred at ambient temperature for 72 hours. The solvent was evaporated under vacuum and the residues diluted with water and extracted into DCM. The combined organic extracts were washed with 1M sodium hydroxide, water and brine, dried with magnesium sulfate and concentrated under vacuum affording 1.37 g (89%) of trans (4-isopropylcarbamoyl-cyclohexyl)-carbamic acid tert-butyl ester as a white solid. LCMS (Method B, ESI): RT=3.07 min, m+H+ MeCN=326.3; 1H NMR (400 MHz, DMSO) δ: 7.50 (d; 1H); 6.66 (d; 1H); 3.78 (m; 1H); 3.13 (m; 1H); 1.94 (m; 1H); 1.78 (d; 2H); 1.66 (d; 2H); 1.37 (s; 9H); 1.31 (m; 2H); 1.11 (m; 2H); 1.01 (d; 6H).

Provenance & Evidence