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. Author manuscript; available in PMC: 2012 Apr 18.
Published in final edited form as: Biometals. 2010 Nov 20;24(2):239–258. doi: 10.1007/s10534-010-9389-y

Scheme 1.

Scheme 1

Synthesis of (S)-4,5-Dihydro-2-[2-hydroxy-3-(3,6-dioxaheptyloxy)phenyl]-4-methyl-4- thiazolecarboxylic Acid (8) and (S)-4,5-Dihydro-2-[2-hydroxy-3-(3,6,9,12-tetraoxatridecyloxy)phenyl]-4-methyl-4-thiazolecarboxylic Acid (10)a

aReagents and conditions: (a) 60% NaH (2.0 equiv), DMSO, CH3[O(CH2)2]2OTs (12, 1.0 equiv), 71% (13) or CH3[O(CH2)2]4OTs (14, 1.0 equiv), 70% (15); (b) CH3OH (aq), pH 6, 70 ºC, 24 h, 93% (8) or 85% (10).