ON1C2C=CC=CC=2N=N1.Cl.[CH3:12][N:13](C)[CH2:14][CH2:15][CH2:16]N=C=NCC.[CH2:23]([O:25][C:26]([C@@H:28]1[CH2:30][C@H:29]1[C:31]([OH:33])=O)=[O:27])[CH3:24].C(N(CC)CC)C.CNCCC>CN(C)C=O>[CH2:23]([O:25][C:26]([C@@H:28]1[CH2:30][C@H:29]1[C:31](=[O:33])[N:13]([CH3:12])[CH2:14][CH2:15][CH3:16])=[O:27])[CH3:24]Add 1-hydroxybenzotriazole (HOBT) (1.46 g, 10.8118 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (2.07 g, 10.8118 mmol) to a solution of crude trans-cyclopropane-1,2-dicarboxylic acid monoethyl ester (1.71 g, 10.8118 mmol) in N,N-dimethylformamide (11 mL). Stir for 30 minutes. Add triethylamine (2.26 mL, 16.2177 mmol) and methylpropylamine (1.11 mL, 10.8118 mmol) and stir for 16 hours. Quench with 10% aqueous potassium carbonate (10 mL) and extract with ethyl acetate (3×50 mL). Combine the organic extracts, wash with 0.1 N aqueous citric acid (30 mL) and 1 N lithium chloride, dry (magnesium sulfate), concentrate and crystallize with xylenes to give the desired compound (1.02 g, 50%).
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