Lithium Hydroxide → HCID 131723119, compound

Participants

Reaction Steps

Methyl 3-[2-[[(4-amidinophenylmethylene)amino]oxy]-1-oxoethylamino]-2-(S)-[n-butyloxycarbonylamino]-propanoate TFA salt (91 mg, 0.17 mmol) was dissolved in 1.5 mL of methanol and 0.51 mL of 1M LiOH was added. After stirring at room temperature for 16 hours, the reaction mixture was evaporated in vacuo and the residue was dissolved in 2 mL of 1:1 CH2Cl2/TFA. This solution was evaporated in vacuo and the residue was purified by preparative HPLC (Dynamax-300A C18 reverse phase column; 21.4×250 mm; 10 ml/min flow rate; 254 nM; gradient: from 100% H2O with 0.05% TFA to 20% H2O and 80% CH3CN with 0.05% TFA in 50 minutes) to yield 63 mg of desired product as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ 9.39 (bs, 2H), 9.2 (bs, 2H), 8.44 (s, 1H), 7.99 (t, 1H), 7.83 (m, 4H), 7.36 (d, 1H), 4.6 (s, 2H), 4.05 (m, 1H), 3.9 (m, 2H), 3.55 (m, 1H), 3.36 (m, 1H), 1.46 (m, 2H), 1.3 (m, 2H), 0.85 (t, 3H); MS (ESI): m/e 408.2 (M+H)+; HRMS (FAB), e/z Calc. for (M+H)+: 408.188309, Found: 408.189211.

Provenance & Evidence