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CAS No. : | 4480-83-5 | MDL No. : | MFCD00006677 |
Formula : | C4H4O4 | Boiling Point : | No data available |
Linear Structure Formula : | CH2OCH2CO2CO | InChI Key : | PIYNUZCGMLCXKJ-UHFFFAOYSA-N |
M.W : | 116.07 | Pubchem ID : | 78232 |
Synonyms : |
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Chemical Name : | Diglycolicanhydride |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
28.6% | With pyridine; dmap; for 3h;Reflux; | [00167] 3 ?-(Oxycarbonyl-(methoxy) acetic acid)-17-(lH-benzimidazol-l-yl)-androsta- 5,16-diene (46): A mixture of 5 (0.1 g, 0.26 mmol), DMAP (0.035 g, 0.28 mmol), diglycolic anhydride (0.1 g, 0.85 mmol) and pyridine (3 mL) was refluxed for 3 hrs. Cooled to room temperature and quenched to water. Precipitate was extracted with EtOAc, dried with Na2S04, evaporated and the residue was purified by FCC [petroleum ether/EtOAc/TEA (9.5:0.3:0.2)] to give 0.05 g (28.6percent) of pure compound 46: mp 214-215 °C; IR (Neat) 2934, 1722, 1456, 1225, 1147 and 745 cm"1; 1H NMR (500 MHz, CDC13) delta 1.01 (s, 3 H, I8-CH3), 1.07 (s, 3 H, 19-CH3), 4.25 (s, 2 H, CH2), 4.26 (s, 2 H, CH2), 4.74 (m, 1 H, 3a-H), 5.45 (br, 1 H, 6-H), 6.00 (m, 1 H, 16- H), 7.32 (m, 2 H, aromatic-Hs), 7.49 (m,lH, aromatic-H), 7.82 (m, 1 H, aromatic-H), 8.06 (s, 1 H, 2' aromatic- H); 13C NMR (500 MHz, CDC13); delta 172.9, 169.9, 147.0, 141.7, 140.0, 134.4, 125.4, 124.2, 123.4, 119.7, 111.6, 75.0, 69.1, 68.8, 56.0, 50.5, 47.4, 38.2, 37.0, 34.9, 31.3, 31.1, 30.5, 27.8, 20.8, 19.4, 16.2. HRMS calcd 527.2516 (C3oH36N205.Na+), found 527.2516. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27%; 27% | In 5,5-dimethyl-1,3-cyclohexadiene; at 120℃; for 6h;Inert atmosphere; | General procedure: The starting 6,7-dimethoxy-3,4-dihydroisoquinolinium perchlorate (1.2 mmol, 0.35 g) was dissolved in water (50 mL) and the resulting suspension was treated with solid sodium hydroxide until pH 10. The resulting mixture was extracted with dichloromethane (3 × 10 mL) and the organic phase was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The obtained free base (0.21 g, 92 %, 1.1 mmol) was dissolved in dry xylene (2.5 mL) and the corresponding anhydride (1.4 mmol) was added. The reaction mixture was heated at 120 C under inert atmosphere for 6 hours. TLC was used to monitor the course of the reaction. Upon completion, the solvent was evaporated under reduced pressure and the resulting crude products were separated and purified by means of column chromatography. The ratio of the cis:trans diastereomers was obtained from the 1H NMR spectra of the crude reaction mixture. |
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