Cl.[OH:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[CH2:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][C:8]1=[O:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:31]([C:33]1[CH:46]=[CH:45][C:36]([CH2:37][N:38]2[C:42]([CH:43]=O)=[CH:41][N:40]=[CH:39]2)=[CH:35][C:34]=1[F:47])#[N:32].CCOC(C)=O>ClCCCl>[C:31]([C:33]1[CH:46]=[CH:45][C:36]([CH2:37][N:38]2[C:42]([CH2:43][N:10]3[CH2:11][CH2:12][N:7]([CH2:6][C:5]4[CH:14]=[CH:15][CH:16]=[C:3]([OH:2])[CH:4]=4)[C:8](=[O:13])[CH2:9]3)=[CH:41][N:40]=[CH:39]2)=[CH:35][C:34]=1[F:47])#[N:32]To a solution of the amine hydrochloride from Step K (theoretically 0.22 mmol) in 2 mL of 1,2-dichloroethane was added 4 Å powdered molecular sieves (100 mg), followed by sodium triacetoxyborohydride (70 mg, 0.33 mmol). The aldehyde from Step G (51 mg, 0.22 mmol) was added, and the reaction was stirred for 16 hours. The reaction was poured into EtOAc, washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The titled product was obtained as a pale yellow foam.
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