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. 2018 Dec 4;10(1):111–116. doi: 10.1021/acsmedchemlett.8b00501

Scheme 1. Synthesis of the Sobetiramide Library.

Scheme 1

Reagents and conditions: Method A: R1 = H, (i) MeOH, H2SO4, (ii) MeOH, amine. Method B: R1 = Bn, (i) CDI, THF, (ii) BCl3, DCM. Method C: R1 = Bn, (i) oxalyl chloride, DCM, (ii) amine, (iii) Pd/C, TES. Method D: R1 = Bn, (i) EDC, HOBT, DIEA, (ii) Pd/C, TES. Method E: R1 = Bn, (i) DCC, NHS, (ii) amine. Note: compound 20 is a secondary amide (−NR2)