[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]([CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:18][C:19]([O:21][CH3:22])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1A mixture of 2 g (7.67 mmol) of 6-chloro-N-cyclopentylpyridine-3-sulfonamide, 0.7 mL (7.67 mmol) of methyl bromoacetate and 1.2 g (8.4 mmol) of K2CO3 in 15 mL of CH3CN is heated for 12 hours at 80° C. After cooling to room temperature, the medium is filtered and the filtrate is concentrated. The residue is taken up in 100 mL of DCM, washed successively with 50 mL of saturated NaHCO3 solution and 50 mL of water, and the organic phase is then dried over Na2SO4, concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with an 8/2 heptane/EtOAc mixture. 2.4 g of methyl N-[(6-chloropyridin-3-yl)sulfonyl]-N-cyclopentylglycinate are obtained in the form of an oil.
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