[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10](N)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:23]1C(Cl)=NC(Cl)=N[C:24]=1Cl.O.C(OCC)(=O)C>CN(C=O)C>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([C:24]#[N:23])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Cbz-Phe-NH2 (4.86 g, 16.29 mmoles) was dissolved in DMF under nitrogen and cooled on ice bath. Cyanuric chloride (1.95 g, 10.59 mmoles) was added with stirring, and the mixture was allowed to warm to rt overnight. Water (100 ml) and ethyl acetate (250 ml) were added to the mixture. The organic phase was separated and washed three times with water (100 ml) and then dried over magnesium sulfate. The material was filtered and concentrated in vacuo to afford Cbz-Phe-CN as a white solid (4.56 g, 99%) HPLC analysis: >99% purity; Retention time 10.1 min.
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