Reaction SMILES: [Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:25][CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[C:13](NC2C=CN(CC(O)=O)N=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].C(Cl)(=O)C(Cl)=O.[CH3:37][C:38]([O:47][Si](CC)(CC)CC)([CH3:46])[CH2:39][N:40]1[CH:44]=[CH:43][C:42]([NH2:45])=[N:41]1.[N:55]1[C:60]([CH3:61])=[CH:59][CH:58]=[CH:57][C:56]=1[CH3:62]>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:25][CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[C:13]([NH:45][C:42]2[CH:43]=[CH:44][N:40]([CH2:39][C:38]([OH:47])([CH3:37])[CH3:46])[N:41]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10].[N:55]1[C:60]([CH3:61])=[CH:59][CH:58]=[CH:57][C:56]=1[CH3:62]
Reactant: CS(=O)(=O)c1ccc([C@@H](CC2CCCC2)C(=O)Nc2ccn(CC(=O)O)n2)cc1Cl
Reactant: CC[Si](CC)(CC)OC(C)(C)Cn1ccc(N)n1
Agent: O=C(Cl)C(=O)Cl
Solvent: ClCCl
Solvent: O
Solvent: Cc1cccc(C)n1
Product: CC(C)(O)Cn1ccc(NC(=O)[C@H](CC2CCCC2)c2ccc(S(C)(=O)=O)c(Cl)c2)n1
Temperature: 0 °C
Reaction time: 1 h

Procedure:
A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (prepared as in PCT WO 2004/052869 A1, Example 1, 214 mg, 0.65 mmol) was dissolved in methylene chloride (10 mL) and N,N-dimethylfomamide (one drop) and cooled to 0° C. To this solution was added dropwise a solution of oxalyl chloride in methylene chloride (2 M solution, 360 μL, 0.71 mmol) which produced gas evolution and it was then stirred at 0° C. for 15 minutes and 1 h at 25° C. After this time, the reaction was concentrated in vacuo to ⅓ of the original volume. In a separate flask, a solution of 1-(2-methyl-2-triethylsilanyloxy-propyl)-1H-pyrazol-3-ylamine (191 mg, 0.71 mmol), 2,6-lutidine (112 μL, 0.97 mmol) and methylene chloride (10 mL) was cooled to 0° C. in an ice bath. To this solution was added the solution of the prepared acid chloride, diluted with another portion of methylene chloride (2 mL), dropwise. After addition was complete the reaction was then allowed to warm to 25° C. and stirred for 16 hours. After this time the reaction was diluted with water (10 mL) and extracted with methylene chloride (3×10 mL) and then dried over sodium sulfate, filtered and concentrated in vacuo. Purification by AnaLogix Intelliflash system (12 g column, 15% ethyl acetate/hexanes to 45% ethyl acetate/hexanes) produced desired product with some 2,6-lutidine present. This material was then dissolved in methylene chloride (20 mL) and washed with an aqueous 1 N hydrochloric acid solution (10 mL). The aqueous layer was then washed with methylene chloride (2×10 mL), the organic layers combined and dried over sodium sulfate, filtered and concentrated in vacuo to afford 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[1-(2-methyl-2-triethylsilanyloxy-propyl)-1H-pyrazol-3-yl]-propionamide (288 mg, 77%) as an off-white foam: [α]31589=−11.7° (c=0.24, methylene chloride); ES-HRMS m/e calcd for C28H44N3O4SSiCl (M+H)+ 582.2583, observed 582.2587; 1H NMR (300 MHz, DMSO-d6) δ ppm 0.51 (q, J=7.8 Hz, 6H, 3×SiCH2), 0.85 (t, J=7.8 Hz, 9H, 3×CH3), 1.02-1.20 (m, 2H, CH2), 1.14 (s, 3 H, CH3), 1.17 (s, 3H, CH3), 1.33-1.81 (m, 8H, 4×CH2), 1.94-2.23 (m, 1H, CH), 3.34 (s, 3H, SO2CH3), 3.89 (s, 2H, NCH2), 3.89-3.97 (m, 1H, ArCH), 6.45 (d, J=2.3 Hz, 1 H, Ar), 7.45 (d, J=2.3 Hz, 1H, Ar), 7.59 (dd, Jo=8.4 Hz, Jm=1.6 Hz, 1H, Ar), 7.70 (d, Jm=1.6 Hz, 1H, Ar), 8.01 (d, Jo=8.4 Hz, 1H, Ar), 10.79 (s, 1H, NH).