Reaction Steps
4-Allyloxy-N-{2-[(2-benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-methyl]-3,7-dioxo-1-propyl-[1,2]diazepan-4-yl}-3,5-dichloro-benzamide (10c) was synthesized from 7c and the diastereomers of 9 by the method and chromatography used to prepare 10a to afford both anti diastereomer (78 mg, 31% yield, lower Rf) and syn diastereomer (129 mg, 52% yield, higher Rf) of the title compound. 1H-NMR (500Hz, CDCl3) for the anti diastereomer: δ 1.00-1.05 (t, 3H), 1.60-1.80 (m, 2H), 2.03-2.18 (m, 1H), 2.23-2.30 (d, 1H), 2.40-2.48 (m, 1H), 2.62-2.78 (m, 1H), 2.90-3.12 (m, 2H), 3.50-3.60 (m, 1H), 4.05-4.25 (m, 3H), 4.48-4.52 (m, 1H), 4.60-4.68 (m, 3H), 4.80-44.85 (d, 1H), 5.08-5.20 (m, 1H), 5.30-5.39 (m, 2H), 5.40-5.45 (d, 1H), 6.08-6.20 (m, 1H), 6.82-6.85 (d, 1H), 7.30-7.45 (m, 6H), 7.85 (s, 2H); for the syn diastereomer: δ 0.94-1.04 (t, 3H), 1.60-1.72 (m, 2H), 1.85-1.93 (m, 1H), 2.31-2.40 (m, 1H), 2.41-2.51 (m, 1H), 2.72-2.82 (m, 1H), 2.83-2.95 (m, 1H), 3.00-3.09 (m, 1H), 3.17-3.30 (m, 1H), 3.99-4.10 (m, 1H), 4.10-4.18 (d, 1H), 4.21-4.30 (d, 1H), 4.58-4.65 (m, 3H), 4.70-4.78 (m, 1H), 4.85-4.90 (d, 1H), 5.05-5.15 (m, 1H), 5.28-5.35 (d, 1H), 5.40-5.45 (d, 1H), 5.53 (d, 1H), 6.08-6.17 (m, 1H), 6.55-6.60 (d, 1H), 6.75-6.80 (d, 1H), 7.27-7.40 (m, 3H), 7.40-7.55 (m, 1H), 7.60-7.70 (m, 1H), 7.73 (s, 2H). Analytical HPLC for diastereomers of the title compound: 10.26 min. LC-MS (ES+) for the mixture of the product: m/e=661, 663 (M+H+).
