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CAS No. : | 60538-15-0 | MDL No. : | MFCD00237276 |
Formula : | C5H12ClNO3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | OZSJLLVVZFTDEY-RFKZQXLXSA-N |
M.W : | 169.61 | Pubchem ID : | 45357980 |
Synonyms : |
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Chemical Name : | (2R,3S)-Methyl 2-amino-3-hydroxybutanoate hydrochloride |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | To a suspension of D-Threonine methyl ester·HCl ((2S,3R)-methyl 2-amino-3-hydroxybutanoate) 70 (1.75 g, 9.61 mmol) in DCM (70 ml), triethylamine (0.97 g, 9.61 mmol, 1.33 ml) was added. The reaction mixture was stirred at RT for 10 min and 4-iodo salicylic acid (<strong>[16870-28-3]2-hydroxy-4-iodobenzoic acid</strong>) 60 (2.45 g, 9.28 mmol) was added. The solution was evaporated by vacuum and re-dissolved in DCM (130 ml). the reaction mixture was cooled to 0 C. and HOBt (125 mg, 0.928 mmol) and DCC (2.39 g, 11.6 mmol) were added. The reaction mixture was stirred overnight at RT and a precipitate of DCU was formed, which was filtered off. The filtrate was evaporated in vacuum and treated with EA (100 ml) and precipitate was filtered off. The organic solution was washed with water (20 ml), saturated NaHCO3 (40 ml), 5% citric acid (40 ml), water (40 ml) and brine (40 ml) and dried over Na2SO4. The organic solvent was evaporated in vacuum to obtain 3.8 g of red oil. The crude product was purified by flash chromatography: SiO2 (80 ml), CHCl3:Hexane (2:1), CHCl3, 2% MeOH in CHCl3, to obtain 2.46 g of the title compound. Yield: 70%. |