[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[OH-].[Na+].[CH2:8]([O:14][C:15](Cl)=[O:16])[CH2:9][CH:10]=[CH:11][CH2:12][CH3:13]>C(OCC)C>[CH2:8]([O:14][C:15](=[O:16])[N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH2:9][CH:10]=[CH:11][CH2:12][CH3:13]Diethylamine (9.1 g, 125 mmol, 1.25 equiv.) was added to a 2%-aqueous NaOH-solution (200 ml) and the resulting mixture was cooled to 0° C. (icebath). At this temperature chloroformic acid hex-3-enyl ester (16.2 g, 100 mmol) in diethyl ether (200 ml) was added over a period of 35 min. After complete addition, the cooling bath was removed and stirring was continued for 1.5 h. The mixture was acidified with 2N aqueous HCl-solution, the phases separated and the organic phase was washed with brine and dried over MgSO4. The crude product was purified via fractionated distillation (74-76° C./0.05 mbar) to yield 18.2 g (92%) of product.
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