(3aR,4R,6S,6aS)-4-(tert-butoxycarbonylaMino)-3-(pentan-3-yl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylic acid CAS#: 316173-28-1; ChemWhat Code: 424996
Identification
| Product Name | (3aR,4R,6S,6aS)-4-(tert-butoxycarbonylaMino)-3-(pentan-3-yl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylic acid |
| IUPAC Name | (3aR,4R,6S,6aS)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-pentan-3-yl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,2]oxazole-6-carboxylate;tert-butylazanium |
| Molecular Structure |  |
| CAS Registry Number | 316173-28-1 |
| EINECS Number | No data available |
| MDL Number | No data available |
| Beilstein Registry Number | No data available |
| Synonyms | (3aR,4R,6S,6aS)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(1′-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]isoxazole-6-carboxylic acid tert-butylamine, tert-butyl ammonium (3aR,4R,6S,6aS)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(1′-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isooxazole-6-carboxylate; CAS Number: 316173-28-1 |
| Molecular Formula | C17H28N2O5 |
| Molecular Weight | 340.415 |
| InChI | InChI=1S/C17H28N2O5/c1-6-9(7-2)13-12-11(18-16(22)23-17(3,4)5)8-10(15(20)21)14(12)24-19-13/h9-12,14H,6-8H2,1-5H3,(H,18,22)(H,20,21)/t10-,11+,12+,14+/m0/s1 |
| InChI Key | XVJTUDPXKCBNKX-FMCLSXCISA-N |
| Canonical SMILES | O=C(OC(C)(C)C)N[C@@H]1C[C@H](C(=O)O)[C@H]2O\N=C(\C(CC)CC)[C@@H]12 |
| Patent Information |
| No data available |
Physical Data
| Appearance | White powder |
| Solubility | No data available |
| Flash Point | No data available |
| Refractive index | No data available |
| Sensitivity | No data available |
Spectra
| No data available |
Route of Synthesis (ROS)
![Route of Synthesis (ROS) of (3aR,4R,6S,6aS)-4-(tert-butoxycarbonylaMino)-3-(pentan-3-yl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylic acid CAS 316173-28-1](https://www.chemwhat.com/wp-content/uploads/2017/12/Route-of-Synthesis-ROS-of-3aR4R6S6aS-4-tert-butoxycarbonylaMino-3-pentan-3-yl-4566a-tetrahydro-3aH-cyclopentadisoxazole-6-carboxylic-acid-CAS-316173-28-1.png)
| Conditions | Yield |
| Stage #1: (3aR,4R,6S,6aS)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(1′-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]isoxazole-6-carboxylic acid tert-butylamine With potassium carbonate; sodium hydroxide In water; acetone Industry scale; Stage #2: dimethyl sulfate In water; acetone at 30 – 45℃; Stage #3: With ammonia In methanol; water; acetone at 0 – 20℃; for 1.25h; Industry scale; Experimental Procedure 3 Synthesis of methyl (3aR,4R,6S,6aS)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(1′-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isooxazole-6-carboxylate (5) 1,1-dimethylethyl ammonium (3aR,4R,6S,6aS)-4-[[(1,1-dimethylethoxy) carbonyl] amino]-3-(1′-ethylpropyl)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isooxazole-6-carboxylate (16) (3210 g, 7.8 mol) was suspended in acetone (4000 g). Potassium carbonate (53.8 g), and an aqueous solution of 30% sodium hydroxide containing 312 g of sodium hydroxide were added to the resulting suspension. 3000 ml of solvent was removed by evaporation, 3000 ml of acetone was added, then, 3000 ml of solvent was removed by evaporation, 3000 ml of acetone was added, and thereafter 4000 ml acetone was removed by evaporation, obtaining a reaction solution substantially free of the odor of tert-butylamine. The reaction solution was cooled down to 30 – 35°C, to which 1060 ml of dimethyl sulfate was added dropwise at a speed to keep the temperature not exceeding 45°C. After completion of the addition, the resulting reaction mixture was stirred at 40 – 45°C for 1.5 hours. The reaction mixture was cooled down to 15 – 20°C, to which was then added 1500 ml of 25% ammonia. After stirring for 30 minutes, 1500 ml of methanol was added, and then the reaction mixture was cooled down to 0 – 5°C. Thereafter, 2240 ml of 25% ammonia was added to the reaction mixture within 45 minutes. The resulting product was collected by filtration, washed with 3000 ml of water, and dried under vacuum at 45 – 50°C. Finally, 2686.2 g of a product was obtained, with a yield of 97.13%. | 97.13% |
Safety and Hazards
| GHS Hazard Statements | Not Classified For more detailed information, please visit ECHA C&L website |
| Source: European Chemicals Agency (ECHA) License Note: Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: “Source: European Chemicals Agency, http://echa.europa.eu/”. Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. License URL: https://echa.europa.eu/web/guest/legal-notice Record Name: (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate URL: https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213446 Description: The information provided here is aggregated from the “Notified classification and labelling” from ECHA’s C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database |
Other Data
| Transportation | Under the room temperature and away from light |
| HS Code | 296200 |
| Storage | Under the room temperature and away from light |
| Shelf Life | 2 years |
| Market Price | USD |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 413.558 |
| logP | 3.534 |
| HBA | 6 |
| HBD | 3 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 123.24 |
| Rotatable Bond (RotB) | 8 |
| Matching Veber Rules | 2 |
| Use Pattern |
| (3aR,4R,6S,6aS)-4-(tert-butoxycarbonylaMino)-3-(pentan-3-yl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylic acid CAS#: 316173-28-1 Used as Peramivir Intermediate. |
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