Structure of 52079-23-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 52079-23-9 |
Formula : | C4H6O3 |
M.W : | 102.09 |
SMILES Code : | O=C1OCC[C@@H]1O |
MDL No. : | MFCD00211245 |
InChI Key : | FWIBCWKHNZBDLS-VKHMYHEASA-N |
Pubchem ID : | 357853 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
With diethylaminosulfur trifluoride; In dichloromethane; | EXAMPLE 1 To a solution of 16.5 g. (0.102 mole) of diethylaminosulfur trifluoride (DAST) in 20 ml. of methylene chloride at -70 C. was added dropwise 3.50 g (0.034 mole) of (-)-2S-hydroxy-4-butyrolactone [J. W. E. Glattfeld and F. V. Sander, J. Amer. Chem. Soc., 43, 2675 (1921)] in 30 ml. of methylene chloride. The mixture was stirred at -70 C. for 1 hr and was warmed to 25 C. and stirred 1 hr. The mixture was slowly poured into saturated aqueous sodium bicarbonate solution at 0 C. The product was extracted with methylene chloride. The organic phase was dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. The residue was purified by column chromatography on 200 g. of silica gel (0.06-0.20 mm) to yield 2R-fluoro-4-butyrolactone, [alpha]D22 +50 (c 1, CHCl3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With water; for 2h;Heating / reflux; | A suspension of enantiopure (S)-alpha-acetoxy-gamma-butyrolactone (5 g, 34.7 mmol) and Amberlite IRA120 (acid form) in H20 (50 mL) was heated to reflux and reaction progress monitored by GCMS. After 2 hours, GCMS indicated complete transformation. The reaction mixture was filtered and evaporated to dryness. Vacuum distillation 0.3-0.4 mbar (b. p. 85-92C) afforded the enantiopure (S)-alpha-hydroxy-gamma-butyrolactone (2.6 g, 76% yield). [alpha]D;25=-66.1. The crude product may also be isolated from the aqueous solution by extraction with CH2CI2 and the pure product alternatively be isolated by column chromatography. Amberlite IRA-120 may be substituted by H2SO4, however with an overall lower yield. |