tert-butyl N-(1-amino-1-oxopropan-2-yl)carbamate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: DL-N-Boc-alanine (5.0 g, 26.4 mmol), di-tert-butylpyrocarbonate (7.9 mL, 34 mmol), and ammonium bicarbonate (2.5 g, 32 mmol) were stirred together in acetonitrile (101 mL). Pyridine (1.3 mL, 16 mmol) was added. The mixture stirred for 12 hours. Water was added and then the acetonitrile was removed in vacuo. The resulting slurry was filtered. The solid was collected, dissolved in methylene chloride and methanol (90:10), dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound (2.7 g, 55%): 1H NMR (400 MHz, d6-DMSO): 7.20 (br s, 1H), 6.90 (br s, 1H), 6.77 (d, 1H), 3.86 (quintet, 1H), 1.37 (s, 9H), 1.15 (d, 3H). the acetonitrile was removed in vacuo The resulting slurry was filtered The solid was collected dissolved in methylene chloride methanol (90:10), dried over sodium sulfate filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: DL-N-Boc-alanine (5.0 g, 26.4 mmol), di-tert-butylpyrocarbonate (7.9 mL, 34 mmol), and ammonium bicarbonate (2.5 g, 32 mmol) were stirred together in acetonitrile (101 mL). Pyridine (1.3 mL, 16 mmol) was added. The mixture stirred for 12 hours. Water was added and then the acetonitrile was removed in vacuo. The resulting slurry was filtered. The solid was collected, dissolved in methylene chloride and methanol (90:10), dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound (2.7 g, 55%): 1H NMR (400 MHz, d6-DMSO): 7.20 (br s, 1H), 6.90 (br s, 1H), 6.77 (d, 1H), 3.86 (quintet, 1H), 1.37 (s, 9H), 1.15 (d, 3H). the acetonitrile was removed in vacuo The resulting slurry was filtered The solid was collected dissolved in methylene chloride methanol (90:10), dried over sodium sulfate filtered concentrated in vacuo