[NH:1]1[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].C(N(CC)CC)C.O.[CH3:28][C:29]([O:32][C:33](ON=C(C1C=CC=CC=1)C#N)=[O:34])([CH3:31])[CH3:30]>CC(C)=O>[N:1]1([C:33]([O:32][C:29]([CH3:31])([CH3:30])[CH3:28])=[O:34])[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]To a solution of L-Pro-L-Phe (1.0 g, 3.8 mmol) and triethylamine (0,794 ml, 5.7 mmol) in 1:1 water:acetone (38 ml) was added Boc-ON (1.13 g, 4.6 mmol), and the reaction mixture stirred at room temperature for 9 hours. Acetone was removed by evaporation under reduced pressure and the resulting aqueous solution diluted with a solution of saturated sodium bicarbonate and then washed with ether. The remaining aqueous phase was acidified to pH 2.0 and extensively extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and concentrated to yield 1.99 g of N-Boc-L-Pro-L-Phe as a white glassy solid.
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