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. 2024 Jun 2;29(11):2616. doi: 10.3390/molecules29112616

Scheme 1.

Scheme 1

Reagents and conditions: (i) (Boc)2O, DMAP, pyridine(anh.), 0 °C–rt, overnight; (ii) 10% KOH(aq), MeOH, reflux, 1 h; (iii) NH4HCO3, HATU, DIEA, DMF, rt, overnight; (iv) TFA, DCM, rt, 1 h; (v) trichloroacetyl isocyanate, THF(anh.), rt, 1.5 h and 4 M NH3 sol. in MeOH, rt, 1.5 h; (vi) p-TSA, acetone, CH3COOH, 80 °C, overnight or p-TSA, appropriate ketone/lactone, toluene(anh.), reflux, overnight; (vii) appropriate acid chloride, pyridine or TEA, DCM, 0 °C–rt, overnight/appropriate sulfonyl chloride, pyridine(anh.), rt, 3 h/appropriate cycloalkyl acid, pyridine(anh.), 50% T3P sol. in EtOAc, DCM(anh.), rt, 1 h/NaH (60% in oil), DMF(anh.), 50 °C, 1 h, (bromomethyl)cyclopropane, 100 °C, overnight; (viii) bis(pinacolato)diboron, CH3COOK, Pd(dppf)Cl2, dioxane(anh.) or DMF(anh.), 80 °C or 100 °C, overnight; (ix) K2CO3, Pd(dppf)Cl2, DMF(anh.), 80 °C, overnight; * substituent.