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. 2015 Oct 12;10(10):e0140006. doi: 10.1371/journal.pone.0140006

Fig 3. Chemical synthesis of apoptozole and derivatives.

Fig 3

Reagents and conditions: i) NH4OAc, AcOH, 100°C, 16 hr; ii) N-Boc-3,6-dioxa-1,8-octanediamine, HBTU, DIPEA, DCM, rt, 5 hr; iii) 1:1 DMC/TFA, rt, 2 hr; iv) 5-FAM NHS ester, NEt3, DMF, rt, 16 hr; v) Cy5 NHS ester, NEt3, DMF, rt, 16 hr; vi) Biotin-derivative 7, HBTU, DIPEA, DMF, rt, 1 hr; vii) Succinic anhydride, DIPEA, MeCN, 30°C, 16 hr, then N-boc-3,6-dioxa-1,8-octanediamine, HBTU, DIPEA, DMF, 35°C, 16 hr; viii) 1:1 DCM/TFA, rt, 16 hr.