[C:1]1([O:7][C:8](=[O:22])[NH:9][C@H:10]([C:14]2[C:19]([F:20])=[C:18]([Cl:21])[CH:17]=[CH:16][N:15]=2)[CH2:11][CH:12]=C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.ClC(OC1C=CC=CC=1)=[O:26]>CO.O1CCOCC1.C(#N)C.CCOC(C)=O>[C:1]1([O:7][C:8](=[O:22])[NH:9][C@H:10]([C:14]2[C:19]([F:20])=[C:18]([Cl:21])[CH:17]=[CH:16][N:15]=2)[CH2:11][CH:12]=[O:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
(S)-Phenyl(1-(4-chloro-3-fluoropyridin-2-yl)but-3-en-1-yl)carbamate: To solution of Intermediate 15B (0.710 g, 1.329 mmol) in MeOH (10 mL) was added 4 M of HCl in dioxane (10 mL) and stirred at rt for 1 h. The reaction mixture was then concentrated and dried under vacuum. The crude product was then re-dissolved in TEA (1.623 mL, 11.65 mmol) and ACN (20 mL). To the above solution was then added phenyl chloroformate (0.321 mL, 2.56 mmol) dropwise and stirred at rt for 10 min. The reaction mixture was diluted with EtOAc and washed with water. The organic layer was concentrated and the residue was purified by silica gel chromatography to yield the desired product (0.550 g, 74%). MS (ESI) m/z: 321.0 (M+H)+.
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