Benzylamine → HCID 11166421, compound

Participants

Reaction Steps

To a solution of 3-[(2R)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]benzoic acid (Preparation 59) (116 mg, 0.22 mmol) in DMF (2 ml) was added triethylamine (62 μl, 0.45 mmol), benzylamine (29 μl, 0.27 mmol), HOBt (33 mg, 0.25 mmol) and WSCDl (47 mg, 0.25 mmol) and the resulting solution stirred at room temperature for 18 hours. The solvent was removed in vacuo and the residue partitioned between saturated aqueous sodium hydrogen carbonate solution (5 ml) and dichloromethane/methanol (95/5) (10 ml). The aqueous layer was separated and extracted with further dichloromethane/methanol (95/5) (4×10 ml). The combined organic layers were dried (sodium sulfate), filtered and evaporated in vacuo. The resulting oil was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (90:10:1, by volume) to give the title compound as a white foam (70 mg). 1H NMR (400 MHz, CD3OD): δ=7.70-7.68 (1H, d), 7.66 (1H, s), 7.38-7.29 (6H, m), 7.26-7.21 (1H, m), 7.21 (1H, s), 7.03-7.01 (1H, d), 6.69-6.67 (1H, d), 4.64-4.61 (1H, m), 4.61 (2H, s), 4.58 (2H, s), 3.05-2.98 (1H, m), 2.92-2.86 (1H, dd), 2.84-2.79 (1H, dd), 2.75-2.71 (1H, dd), 2.68-2.63 (1H, dd), 1.10-1.08 (3H, d) ppm. LRMS (electrospray): m/z [M+H]+ 435, [M+Na]+ 457, [M−H]− 433. CHN analysis: found C, 69.79; H, 6.96; N, 6.37; C26H30N2O4+0.7H2O requires C, 69.84; H, 7.08; N, 6.26.

Provenance & Evidence