HCID 70045307, compound → HCID 86748804, compound

Participants

Reaction Steps

To a solution of 188 mg of N-(3-phenylpropionyl-valinyl-alaninyl)-4-amino-5-benzyloxy-2-oxo-tetrahydrofuran in 2 mL of dimethylformamide and 3 mL of methanol was added ~100 mg of Pd(OH)2 on carbon. After the mixture had been stirred vigorously under hydrogen for 3 hours, the mixture was filtered through a 0.22 μm nylon membrane filter and concentrated. The residue was purified by MPLC on silica-gel (22×300 mm column, eluted with a gradient of dichloromethane to 8% formic acid and 32% methanol in dichloromethane) to afford 112 mg of the title compound as a colorless solid: 1H NMR (400 MHz, CD3OD (1:1 mixture of diastereomeric hemiacetals in this solvent)) δ7.3-7.1 (m, 5H, Ar--H), 4.58 (d, 0.5H, J=4.06 Hz, CH(OH)(OCD3)), 4.56 (d, 0.5H, J=3.96 Hz, CH(OH)(OCD3)), 4.34 (m, 1H, CHN), 4.24 (m, 1H, CHN), 4.02 (d, 1H, J=7.38 Hz, CHN), 2.91 (t, 2H, J=7.61Hz, CH2CON), 2.7-2.4 (m, 4H, CH2Ph, CH2CO2), 2.00 (m, 1H, CH(CH3)2), 1.32 (d, 3H, J=7.10 Hz, CHCH3), 0.88 (d, 3H, J=6.82 Hz, CH(CH3)2), 0.85 (d, 3H, J=6.83 Hz, CH(CH3)2).

Provenance & Evidence