[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]([CH:16]1[CH2:21][CH2:20][CH:19]([C:22](O)=[O:23])[CH2:18][CH2:17]1)=[O:15].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH2:9][CH2:10][NH:11][C:22]([CH:19]2[CH2:18][CH2:17][CH:16]([C:14]([O:13][CH3:12])=[O:15])[CH2:21][CH2:20]2)=[O:23])=[CH:6][CH:7]=1
To a solution of 2-[(4-chlorophenyl)sulfanyl]ethanamine (12.2 g, 542 mmol) in DMF (350 ml) was added sequentially 4-(methoxycarbonyl)cyclohexanecarboxylic acid (cis/trans mixture), EDC (11.4 g, 59.7 mmol) and HOAt (1.48 g, 10.9 mmol) at room temperature followed by Et3N (17.39 ml, 125 mmol). The reaction was stirred overnight at ambient temperature, diluted with water and extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and conc. The residue was purified by silica gel flash chromatography (0-70% EtOAc in heptane) to afford the product. LCMS: M+H=356.1.
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