Benzylamine → (3S*,4R*)-3-benzylcarbamoyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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To a stirring solution of (3S*,4R*)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (70 mg, 0.138 mmol), bis(2-oxo-3-oxazolidinyl)phosphinic chloride (42 mg, 0.166 mmol) and triethylamine (77 μL, 0.552 mmol) in CH2Cl2 (3 mL), benzylamine (18 μL, 0.166 mmol) is added. The resulting solution is refluxed for 2 h and then quenched by the addition of aqueous NaHCO3 solution. The organic layer is separated, and the aqueous phase is extracted 3 times with CH2Cl2. The combined organic extracts are dried (Na2SO4), and the solvent is removed in vacuo. The crude material is purified by preparative HPLC (C18-ODB-AQ, 5 μm, 20×50 mm, YMC, eluent: CH3CNIH2O+0.1 % HCOOH flow: 20 mL/min). The HPLC fractions are collected and lyophilized to afford the title product. TLC, Rf (CH2Cl2/MeOH 95:5)=0.2. MS (LC-MS): 598.0 [M+H]+; tR (HPLC, C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 5.60 min.

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