FC(F)(F)C(O)=O.[CH3:8][NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]#[C:17][CH2:18][O:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:12][CH2:11]1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1.N1C=CC=CC=1>O1CCOCC1.OS([O-])(=O)=O.[K+].CCOCC>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:33])[N:9]([C@H:10]2[CH2:11][CH2:12][C@H:13]([C:16]#[C:17][CH2:18][O:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:14][CH2:15]2)[CH3:8])=[CH:27][CH:26]=1A solution of 1.38 g (corresponds to 3.0 mmol) of trans-Methanesulfonic acid 3-(4-methylamino-cyclohexyl)-prop-2-ynyl ester trifluoroacetate in 7 ml dioxane was first cooled to 8° C., treated with 0.69 g (4.5 mmol) 4-chlorophenyl isocyanate and then with 1.2 ml (15 mmol; 5 equivalents) of pyridine (during 3 min). After 45 min at RT, the mixture was dissolved in aqueous 10% KHSO4/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried over Na2SO4 and evaporated to give 1.22 g (quantitative) of crude trans-Methanesulfonic acid 3-{4-[3-(4-chloro-phenyl)-1-methyl-ureido]-cyclohexyl}-prop-2-ynyl ester, MS: 398 (MH+, 1Cl). The crude product was directly used in the next step.
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