C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([S:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][CH:22]=1)[CH2:17][CH2:18][CH3:19].[C:30]([C:32]1[CH:37]=[CH:36][C:35]([SH:38])=[CH:34][CH:33]=1)#[N:31]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:16]([S:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([S:38][C:35]2[CH:36]=[CH:37][C:32]([C:30]#[N:31])=[CH:33][CH:34]=2)=[O:27])=[CH:28][CH:29]=1)[CH2:17][CH2:18][CH3:19]N,N'-dicyclohexylcarbodiimide (0.99 g, 0.005 mol), was added in one portion to a stirred solution of compound 2 (1.04 g, 0.005 mol), compound 10 (0.56 g, 0.004 mol) and 4-(dimethylamino)pyridine (0.20 g, 0.002 mol), in dry dichloromethane (50 ml) at room temperature. The reaction mixture was stirred at room temperature overnight. The product was extracted into ether (200 ml) and was washed with aqueous potassium hydroxide solution (5%, 2×250 ml). The ether layer was evaporated in vacuo and the product was purified by column chromatography [silica gel/petroleum fraction (bp 40°-60° C.), dichloromethane, 1:1] and was recrystallised from ethanol to afford a white solid which was dried in vacuo (P2O5).
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