Hydrochloric Acid → HCID 86663710, compound

Participants

Reaction Steps

A solution of (R)-2-tert-butoxycarbonylamino-2-(2-pyrrolidin-1-yl-ethyl)-6-(4,4,5,5-tetramethyl-[1,3,2]-dioxa-borolan-2-yl)-hexanoic acid ethyl ester (98 mg) in 6 N hydrochloric acid (5 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 2-amino-6-borono-2-[2-pyrrolidin-1-yl)-ethyl]-hexanoic acid dihydrochloride, as a colorless foam (36 mg, 53%); 1H NMR (D2O, 300 MHz) δ 3.47 (m, 2H), 3.24 (m, 1H), 3.07 (m, 1H), 2.88 m, 2H), 2.12 (t, J=8 Hz, 2H), 1.94 (m, 2H), 1.60-1.82 (m, 4H), 1.20 (m, 3H), 1.04 (m, 1H) and 0.59 (t, J=7 Hz, 2H); MS (+CI): m/z for C12H25BN2O4: expected 272.2. found 273.2 (M+H)+.

Provenance & Evidence