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. 2018 Oct 19;3(10):13647–13666. doi: 10.1021/acsomega.8b01481

Scheme 3. Synthesis of N-Boc-3-(Thiazol-5-yl)-l-alanine 4b.

Scheme 3

Reagents and conditions: (a) TMS-Cl, n-BuLi, Et2O, −78 °C, 89%; (b) N-formylmorpholine, Et2O, −78 °C, 50%; (c) NaBH4, MeOH, rt, 61%; (d) SOCl2 neat, rt, quant; (e) diethyl acetamidomalonate, NaOEt, KI, EtOH, reflux, 71%; (f) (1) aq. NaOH; (2) aq. HCl, reflux, 52%; and (g) (1) aq. NaOH; (2) aminoacylase, 37 °C, pH 7.3; (3) Boc2O, THF, rt, 44%.