Chemical Properties
WHITE AMORPHOUS POWDER
Uses
N-Boc-L-threonine is an N-Boc-protected form of L-Threonine (T405500). L-Threonine is an essential amino acid that is commonly used as a feed and food additive. L-Threonine is produced in mass quantities by mutant Escherichia coli strains for research and food nutrition purposes. L-Threonine can be naturally found in fish and poultry, and is incorporated in some important proteins in the human body (such as hemoglobin and insulin).
reaction suitability
reaction type: Boc solid-phase peptide synthesis
Synthesis
The general procedure for the synthesis of (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxybutyric acid from L-threonine and di-tert-butyl dicarbonate was as follows:
1. To a methanol (5 mL) solution of L-threonine (400 mg, 3.36 mmol), a water (5 mL) solution of sodium bicarbonate (434 mg, 5.17 mmol) was added, followed by di-tert-butyl dicarbonate (1.07 g, 4.90 mmol).
2. The reaction mixture was stirred at room temperature for 3 days.
3. Upon completion of the reaction, the solvent was removed by vacuum distillation. 4.
4. The residue was diluted with water (20 mL) and washed with ether (2 x 20 mL).
5. The aqueous layer was acidified with saturated aqueous sodium bisulfite and then extracted with 2-methyltetrahydrofuran.
6. The organic layer was dried over anhydrous sodium sulfate and subsequently concentrated in vacuo to afford the title compound (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxybutyric acid as a white solid (730 mg, 99% yield).
7. The product was characterized by 1H NMR (400 MHz, CDCl3) and LC-MS: 1H NMR δ 1.24 (d, 3H), 1.44 (s, 9H), 4.26 (d, 1H), 4.40 (d, 1H), 5.52 (d, 1H), 5.69 (br s, 1H); LCMS Rt = 1.68 min, MS m/z 218 [M + H]+.
References
[1] Patent: WO2013/114250, 2013, A1. Location in patent: Page/Page column 161; 162
[2] Patent: WO2013/110643, 2013, A1. Location in patent: Paragraph 00118; 00119
[3] Advanced Synthesis and Catalysis, 2014, vol. 356, # 8, p. 1795 - 1802
[4] Patent: CN102993200, 2016, B. Location in patent: Paragraph 0043; 0044; 0045
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5770 - 5781
