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CAS No. : | 10326-41-7 | MDL No. : | MFCD00068313 |
Formula : | C3H6O3 | Boiling Point : | - |
Linear Structure Formula : | (HO)CH(CH3)COOH | InChI Key : | JVTAAEKCZFNVCJ-UWTATZPHSA-N |
M.W : | 90.08 | Pubchem ID : | 61503 |
Synonyms : |
|
Chemical Name : | (R)-2-Hydroxypropanoic acid |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501 | UN#: | 3261 |
Hazard Statements: | H314 | Packing Group: | Ⅲ |
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 |
---|---|---|
42.7% | In water; ethyl acetate; butan-1-ol; at 10 - 70℃; for 17h;Resolution of racemate; | Ten grams (10 g, 78.0 mmol) of <strong>[4138-26-5]nipecotamide</strong> was dissolved in a mixed solvent of 30 mL of 1-butanol and 30 mL of ethyl acetate. To the solution was added 8.53 g (98.6percent ee, 90percent aqueous solution, 85.8 mmol) of D-lactic acid, and the solution was stirred at 70° C. To the reaction mixture was added a small amount of D-lactic acid salt of R-<strong>[4138-26-5]nipecotamide</strong>, which was prepared in advance, as a seed crystal, and a diastereomer salt was precipitated. The reaction mixture was stirred for 1 hour at the same temperature, and then was cooled to 10° C. while stirring for 6 hours. The mixture was further stirred for 10 hours. The precipitated diastereorner salt was filtered and collected. The diastereomer salt was washed with a mixed solvent of 10 mL of 1-butanol and 10 mL of ethyl acetate at approximately 5° C. After drying, the obtained white diastereomer salt weighed 7.27 g. The diastereomer salt was D-lactic acid salt of R-<strong>[4138-26-5]nipecotamide</strong>, and the yield was 42.7percent. The optical purity of R-<strong>[4138-26-5]nipecotamide</strong> obtained from the diastereomer salt was analyzed and was found to be 98.0percent ee.1H-NMR (DMSO-d6, 400 MHz) deltappm: 7.47 (1H, s), 6.95 (1H, s), 3.71 (1H, q, J=13.7, 6.8 Hz), 3.14-3.02 (2H, m), 2.80-2.64 (2H, m), 2.54-2.44 (1H, m), 1.90-1.84 (1H, m), 1.74-1.67 (1H, m), 1.62-1.43 (2H, m), 1.14 (3H, d, J=6.8 Hz). |
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