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. 2019 Feb 14;62(7):3254–3267. doi: 10.1021/acs.jmedchem.8b01719

Scheme 1. Representative Synthesis of Oxazolidinone 18.

Scheme 1

Conditions: (i) NBS, CCl4, benzoyl peroxide, reflux, 4 h, 71%; (ii) aniline 14, DMF, 85 °C, 47%; (iii) LiBH4, THF, 84%; (iv) triphosgene, Et3N, DCM, 50%; (v) (BPin)2, PdCl2(dppf)·CH2Cl2, KOAc, dioxane, 100 °C; and (vi) PS-BBA, HCl, THF, 30% for 2 steps.