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. 2018 Apr 12;9(5):434–439. doi: 10.1021/acsmedchemlett.8b00008

Scheme 3. Syntheses of 14.

Scheme 3

Reagents and conditions: (a) (S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate, PivCl and pyridine for 0.5 h at rt, 90–95%; (b) (R)-tert-butyl 2-(tert-butoxycarbonyl)amino)-3-hydroxypropanoate, PivCl and pyridine for 0.5 h at rt, 90–98%; (c) (i) I2 and 95% pyridine-H2O at rt; (ii) TFA and CH2Cl2 at 0 °C, 98%.