C(O)C.[Na].[C:5]1([CH2:11][C:12](=[NH:14])[NH2:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:15]([N:22]1[CH2:28][CH2:27][C:26](=O)[CH:25]([C:30](OCC)=[O:31])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH2:11]([C:12]1[NH:14][C:30](=[O:31])[C:25]2[CH2:24][CH2:23][N:22]([CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:28][CH2:27][C:26]=2[N:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1Ethanol (50 ml) was cooled in an ice bath then sodium (442 mg, 19.2 mmol) added, with vigorous stirring. Once the sodium was dissolved, 2-phenylethanimidamide (1.29 g, 9.6 mmol) and ethyl 1-benzyl-5-oxoazepane-4-carboxylate (2.5 g, 8 mmol) was added. The reaction mixture was refluxed, under nitrogen, for 17 h. Water (10 ml) was added to quench the reaction then the reaction mixture concentrated in vacuo. The residue was partitioned between ethyl acetate (200 ml) and water (200 ml). The organic phase was dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with DCM:MeOH (98:2 to 95:5), to afford a white solid, 1.35 g, 49%
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