Diisopropylethylamine → HCID 57695553, compound

Participants

Reaction Steps

To a solution of 4,6-bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid (4.4 g, 9.2 mmol), diisopropylethylamine (3.2 ml, 18.3 mmol) and HBTU (5.2 g, 13.7 mmol) in anhydrous DMF (44 ml) was charged 4-amino-1-N-Boc-piperidine (2.3 g, 11.4 mmol). The mixture was stirred at rt for 16 h. The reaction mixture was then diluted with ethyl acetate and washed with water. The organics were then dried (Na2SO4), filtered and evaporated to yield 4-[(4,6-bis-benzyloxy-5′isopropyl-2′methoxy-biphenyl-3-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester as a brown solid (6.1 g, quant.), carried forward without further purification. M.p.: 168-170° C.; 400 MHz 1H NMR (CDCl3) δ: 8.16 (s, 1H), 7.79 (d, J=7.6 Hz, 1H), 7.42 (s, 4H), 7.34-7.26 (m, 6H), 7.18 (dd, J=8.4, 2.0 Hz, 1H), 7.14 (s, 1H), 6.87 (d, J=8.4 Hz, 1H), 6.64 (s, 1H), 5.12 (s, 2H), 5.05 (s, 2H), 4.07 (m, 1H), 3.73 (s, 3H), 3.56 (br s, 2H), 2.90 (m, 2H), 1.78 (d, J=7.2 Hz, 2H), 1.57 (s, 1H), 1.47 (s, 9H), 1.24 (d, J=7.2 Hz, 6H), 1.08 (m, 2H); LCMS: 576 [M+H].

Provenance & Evidence