[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[C:10]([OH:13])([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[CH3:19][NH:20][CH3:21].C(N(C(C)C)C(C)C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C=O)C.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([N:20]([CH3:21])[CH3:19])=[O:16])[C:10]([OH:13])([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]To a solution of N-(tert-butoxycarbonyl)-3-hydroxy-L-valine (1.00 g), 2M dimethylamine methanol solution (2.14 mL) and N-ethyl-N-(1-methylethyl)propan-2-amine (1.11 g) in DMF (10 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.63 g) at room temperature. The reaction mixture was stirred at room temperature overnight. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (670 mg).
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