[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](O)=[O:18])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[BH4-].[Na+]>C1COCC1.C(OCC)(=O)C.CCCCCCC>[OH:18][CH2:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:10][CH:11]=13-{4-[(tert-Butoxycarbonyl)amino]phenyl}propanoic acid (1.33 g, 5.013 mmol) and BOP reagent (2.882 g, 6.517 mmol) were mixed in THF (30 ml). DIPEA (907 mg, 7.018 mmol) was added. The mixture was stirred for 10 minutes. Sodium borohydride (246 mg, 6.517 mmol) was added. The mixture was stirred for 30 minutes more and then evaporated to dryness. Ethyl acetate and water were added into the residue. The organic phase was washed with water and brine and dried with magnesium sulfate. The solvent was evaporated and an oil mixture was obtained. Column chromatography of the oil on silica gel using ethyl acetate/heptane (10:90, then 25:75) as eluant gave the desired oil product (616 mg), yield 49%.
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