Cl.[CH3:2][O:3][C:4]([C:6]1([NH2:11])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].C(N(CC)C(C)C)(C)C.[C:21]([O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1)#[C:22][CH2:23][CH3:24]>C(Cl)Cl.C(#N)C>[CH2:21]([O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:11][C:6]2([C:4]([O:3][CH3:2])=[O:5])[CH2:10][CH2:9][CH2:8][CH2:7]2)(=[O:34])=[O:33])=[CH:28][CH:27]=1)[C:22]#[C:23][CH3:24]To a stirred suspension of methyl-1-amino-1-cyclopentane carboxylate hydrochloride (15 g, 84.0 mmol) and N,N-diisopropylethylamine in methylene chloride (200 mL) and acetonitrile (50 mL), 4-butynyloxyphenylsulfonylchloride (24.7 g, 100 mmol) was slowly added at room temperature. Reaction mixture was stirred for 16 hrs and evaporated to dryness. It was extracted with chloroform, washed well with water and dried over anhydrous MgSO4. Chloroform layer was filtered and concentrated. The product was crystallized from a mixture acetone:hexane (1:1) to give methyl 1-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)cyclopentane carboxylate as white crystals, 26.8 g (91%), mp 81-3° C. Electrospray Mass Spec352 (M+H)+.
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