Trifluoroacetic acid → 4-methyl-D-leucyl-N1-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-N2-cyclopropylglycinamide

Participants

Reaction Steps

TFA (3 mL) was added to a solution of N-(tert-butoxycarbonyl)-4-methyl-D-leucyl-N1-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-N2-cyclopropylglycinamide (80 mg, 0.15 mmol) in CH2Cl2 (6 mL). The solution was stirred at room temperature for 30 min and the solvent was then removed in vacuo. The residue was taken up in DMF and purified by reverse phase HPLC. The product fractions were combined and reduced in vacuo and the residual oil was concentrated repeatedly from Et2O to give the title compound as a white foam. 1H NMR (500 MHz, CD3O): δ 9.52 (s, 1 H), 8.50 (m, 1 H), 7.68 (d, J=2.5 Hz, 1 H), 7.57 (dd, J=2.5, 8.5 Hz, 1 H), 7.50 (d, J=8.0 Hz, 1 H), 4.72 (dd, J=3.5, 8.5 Hz, 1 H), 4.28 (d, J=16.0 Hz, 1 H), 4.24 (d, J=15.5 Hz, 1 H), 4.10 (d, J=16.0 Hz, 1 H), 3.99 (d, J=16.0 Hz, 1 H), 2.91–2.86 (m, 1 H), 2.02 (dd, J=3.5, 15.5 Hz, 1 H), 1.70 (dd, J=8.5, 15.0 Hz, 1 H), 1.06 (s, 9 H), 1.03–0.86 (m, 4 H). HRMS (APCI, M+H): 434.2055 (found); 434.2066 (calculated).

Provenance & Evidence