[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]2)=[O:11])=[N:4][CH:5]=[CH:6][N:7]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:19]([O:18][C@H:15]1[CH2:16][CH2:17][C@H:12]([C:10](=[O:11])[NH:9][CH2:8][C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:13][CH2:14]1)(=[O:21])[CH3:20]The total harvest of (trans)-N-((3-chloropyrazin-2-yl)methyl)-4-hydroxycyclohexanecarboxamide (10 mmol, 2.7 g) and 4-dimethylaminopyridine (1.0 mmol, 0.12 g) were dissolved in pyridine (25 ml), acetic anhydride (10.51 mmol, 0.994 ml) was added and the mixture was stirred at room temperature. After 1 hour the reaction was quenched in 185 mL of 2N hydrochloric acid (pH becomes four) and extracted with ethyl acetate three times. The combined organic layers were dried (sodium sulfate) and concentrated to give 2.8 g of (trans)-4-((3-chloropyrazin-2-yl)methylcarbamoyl)cyclohexyl acetate.
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