Lithium Hydroxide → 2-(2-((tert-Butoxycarbonyl)(methyl)amino)-N-methylacetamido)acetic acid

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Reaction Steps

A suspension of {[2-(tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetic acid ethyl ester (12.3 g, 42.7 mmol) and LiOH (8.9 g, 214 mmol) in H2O (20 mL) and THF (100 mL) was stirred overnight. Volatile solvent was removed under vacuum and the residue was extracted with ether (2×100 mL). The aqueous phase was acidified to pH 3 with dilute HCl solution, and then extracted with CH2Cl2 (2×300 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under vacuum to give {[2-(tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetic acid as a colorless oil (10 g, 90%). 1H NMR (CDCl3) δ 7.17 (br s, 1 H), 4.14-4.04 (m, 4 H), 3.04-2.88 (m, 6H), 1.45-1.41 (m, 9 H); ESI-MS 282.9 m/z (M+Na+).

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