[C:1]([N:8]1[CH2:11][C:10](=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[F:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.[C:21](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[F:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][CH:10]2[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]2)=[C:16]([CH3:21])[CH:15]=1A solution of 1-Boc-3-azetidinone (800 mg, 4.67 mmol), 4-fluoro aniline (0.519 ml, 4.67 mmol), acetic acid (0.535 ml, 9.34 mmol) and sodium(triacetoxy)borohydride (1.98 g, 9.34 mmol) in 1,2-dichloroethane (20 ml) was stirred under N2 atmosphere at room temperature for 1 day. Sat. solution of NaHCO3 (25 ml) was added. After phase separation, the aqueous layer was extracted with dichloromethane (2×35 ml). The collected organics after solvent evaporation were purified by Biotage SNAP-Si cartridge (25 g) eluting with cyclohexane/ethylacetate from 90/10 to 80/20. Collected fractions after solvent evaporation afforded the title compound (D30) (880 mg)
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