Uses
tert-Butyl
N-(2,3-dihydroxypropyl)carbamate may be used in the preparation of isobaric mix solution for use in post-column infusion experiment during single-stage orbitrap mass spectrometric analysis.
General Description
tert-Butyl
N-(2,3-dihydroxypropyl)carbamate is a protected amine.
Synthesis
GENERAL STEPS: 3-Amino-1,2-propanediol (3 g, 32.93 mmol, 1.0 eq.) was dissolved in a mixture of 20 mL of tert-butanol and 20 mL of 1 M NaOH. A 20 mL solution of tert-butanol containing di-tert-butyl dicarbonate (7.19 g, 32.93 mmol, 1.0 eq.) was slowly added under ice bath cooling conditions. The reaction mixture was stirred at room temperature for 5 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the complete consumption of the raw materials, the reaction solution was concentrated under reduced pressure in a 50 °C water bath. Subsequently, the reaction mixture was neutralized with 1 M HCl solution. The neutralized solution was subjected to liquid-liquid extraction with ethyl acetate and water, which was repeated three times. The organic layers were combined, washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The dried organic phase was concentrated under reduced pressure in a water bath at 40 °C to give 6.3 g of tert-butyl N-(2,3-dihydroxypropyl)carbamate (yield: quantitative). The structure of the product was confirmed by 1H-NMR: 1H-NMR (500 MHz, CDCl3) δ 1.45 (9H, s), 2.68-2.71 (1H, br), 2.75-2.81 (1H, br), 3.20 (2H, dd), 3.63 (2H, dd), 3.71 (1H, m), 4.91 (1H, br).
References
[1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 2, p. 623 - 627
[2] Patent: US2016/151506, 2016, A1. Location in patent: Paragraph 0308-0312
[3] Canadian Journal of Chemistry, 1997, vol. 75, # 7, p. 942 - 948
[4] Patent: US2006/69156, 2006, A1. Location in patent: Page/Page column 26
[5] Patent: US2006/154984, 2006, A1. Location in patent: Page/Page column 41
