N-(tert-butoxycarbonyl)glycine → N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester

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Reaction Steps

Boc-Gly-OH (1.54 g, 8.82 mmol) was put in a 500-mL eggplant flask and dissolved in distilled CHCl3. Then, DCU (2.18 g, 10.6 mmol) and HOSu (1.21 g, 10.6 mmol) were added thereto, and the stirring was started under cooling. After having been left standing overnight, the completion of the reaction was confirmed with TLC and the resultant was concentrated. After filtered, DCUrea was dissolved in AcOEt and the reprecipitated DCUrea was filtered. After that, the filtrate was concentrated and recrystallized with AcOEt-distilled Et2O twice, whereby Boc-Gly-OSu was obtained. The yield was 1.74 g (63.9%). 1H NMR (CDCl3, 300 MHz): 5.04 (1H, Boc-Gly NH); 4.27, 4.23 (2H, Gly αCH2); 2.79 (4H, OSu); 1.40 (9H, Boc t-Bu).

Provenance & Evidence