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CAS No. : | 1148-11-4 | MDL No. : | MFCD00003170 |
Formula : | C13H15NO4 | Boiling Point : | 432.3°C at 760 mmHg |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 249.26 g/mol | Pubchem ID : | 101987 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With pyridine; di-<i>tert</i>-butyl dicarbonate; ammonium bicarbonate In 1,4-dioxane at 20℃; | To a solution of starting 1-[(phenylmethyl)oxy]carbonyl}-L-proline (8.0 g, 32.09 mmol), pyridine (1.5 mL), (BoC)2O (9.1 g, 41.72 mmol) in 1 ,4-dioxane (40 ml_) at rt was added ammonium hydrogen carbonate (3.2 g, 40.43 mmol). After stirring at room temperature overnight, the reaction mixture was treated with EtOAc (100 mL), and then the mixture was washed with water (50 mL), followed by 5percent H2SO4- The organic layer was collected, dried(Na2SO4), filtered. The volatiles were removed by evaporation in vacuo. The resulting clear oil was triturated with ether. The precipitates were filtered and further dried under vacuum to yield the title compound as a white solid (3.9 g, 49percent). MH+ 249. |
13.5 g | Stage #1: With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at -5℃; for 0.333333 h; Stage #2: With ammonium hydroxide In tetrahydrofuran at -5 - 20℃; for 18 h; |
Step A - Syntheses of Intermediate Compound Int-13b (0313) (0314) Ethyl chloroformate (12 mL, 125 mmol) in 180 mL of THF was added drop-wise to a cooled solution (-5°C) of compound Z-Pro-OH (13.8 g, 55.5 mmol), TEA (7.71 mL, 55.5 mmol). The resulting slurry was allowed to stir for 20 minutes at -5°C before saturated NH4OH (15 mL) was added. The solution was allowed to stir at room temperature for 18 hours, volatiles were removed, and the resulting residue was taken up in EtOAc (180 mL). The undissolved white precipitate was filtered off and rinsed with EtOAc (100 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo to provide the desired product (13.5 g) as off-white amorphous solid (Int-13b). MS (ESI) m/e (M+H+): 249 |
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