Hydrochloric Acid → HCID 66833498, compound

Participants

Reaction Steps

2-Amino-6-borono-2-[2-(4-pyrimidin-2-yl-piperazin-1-yl)ethyl]-hexanoic acid trihydrochloride is prepared in a manner analogous to that set forth in Example 16, except 1-2-(1-piperidinyl)pyrimidine is used as the amine in step 6. The final step is as follows: a solution of (R/S)-2-tert-butoxycarbonylamino-2-[2-(4-pyrimidin-2-yl-piperazin-1-yl)-ethyl]-6-(4,4,5,5-tetramethyl-[1,3,2]-dioxa-borolan-2-yl)-hexanoic acid ethyl ester (126 mg) in 6 N hydrochloric acid (6 mL) was stirred at 95° C. overnight. After cooling to room temperature, the reaction mixture was transferred to a separatory funnel, diluted with deionized water (5 mL) and washed with dichloromethane (3×). The aqueous layer was frozen in liquid nitrogen and lyophilized to give the title compound as a white solid (80 mg, 83%); 1H NMR (D2O, 300 MHz) δ 8.47 (d, J=5.5 Hz, 2H), 6.96 (t, J=5.5 Hz, 1H), 3.48-3.76 (m, 4H), 3.14-3.40 (m, 6H), 2.29 (t, J=8 Hz, 2H), 1.81 (m, 2H), 1.28 (m, 3H), 1.11 (m, 1H) and 0.62 (t, J=7.5 Hz, 2H).

Provenance & Evidence