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| | (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid Basic information |
| Product Name: | (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid | | Synonyms: | (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid;(2E,4R)-5-[1,1'-biphenyl]-4-yl-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-2-Pentenoic acid;5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methyl-pent-2-enoic acid;2-Pentenoic acid, 5-[1,1'-biphenyl]-4-yl-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-, (2E,4R)-;(R,E)-5-(biphenyl-4-yl)-4-(tert-butoxycarbonylamino)-2-methylpent-2-enoic acid;(R,E)-5-(biphenyl-4-yl)-4-(tert-butoxycarbonylamino);(2E,4R)-5-[1,1'-Biphenyl]-4-yl-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-2-pentenoic acid AHU83;1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid | | CAS: | 1012341-48-8 | | MF: | C23H27NO4 | | MW: | 381.46 | | EINECS: | 695-654-2 | | Product Categories: | LCZ696;intermediate;intermediates;1012341-48-8 | | Mol File: | 1012341-48-8.mol | ![(R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid Structure](CAS/20150408/GIF/1012341-48-8.gif) |
| | (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid Chemical Properties |
| Melting point | 188 - 191°C | | Boiling point | 595.6±50.0 °C(Predicted) | | density | 1.132±0.06 g/cm3(Predicted) | | vapor pressure | 8.4-839.931Pa at 20℃ | | storage temp. | Sealed in dry,Room Temperature | | solubility | DMSO (Slightly), Methanol (Slightly) | | form | Solid | | pka | 4.67±0.19(Predicted) | | color | White to Off-White | | InChI | InChI=1S/C23H27NO4/c1-16(21(25)26)14-20(24-22(27)28-23(2,3)4)15-17-10-12-19(13-11-17)18-8-6-5-7-9-18/h5-14,20H,15H2,1-4H3,(H,24,27)(H,25,26)/b16-14+/t20-/m0/s1 | | InChIKey | JXTNUXJSXXIIFE-VISDOYDDSA-N | | SMILES | C(O)(=O)/C(/C)=C/[C@H](NC(OC(C)(C)C)=O)CC1=CC=C(C2=CC=CC=C2)C=C1 | | LogP | 2.2-3.6 at 25℃ and pH2.5-7 |
| | (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid Usage And Synthesis |
| Uses | (R,E)-5-([1,1-Biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-methylpent-2-enoic Acid is used in preparation of sacubitril intermediate using Nickel Salt catalyst. | | Synthesis | The general procedure for the synthesis of (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methyl-2-pentenoic acid from ethyl (4R)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methyl-2-pentenoic acid was as follows:
Step 1: 800 g of 95% ethanol and 400 g of pure water were mixed, compound I (1.3 mol) and lithium hydroxide (0.1833 mol) were added, and the reaction was held at reflux for 1 hour at 80 °C. After completion of the reaction, it was cooled to room temperature, activated carbon was added, heated to 42 °C and then continued to raise the temperature to 80 °C reflux. Incubate at room temperature for 2 hours.
Step 2: The reaction mixture was thermally filtered and aqueous citric acid was added to the filtrate to terminate the reaction. Subsequently, the mixture was heated at reflux at 80°C for 1 hour and cooled to room temperature to crystallize. The crystals were collected by filtration and dried to give 55.4 g of dry Compound II in 79.05% molar yield and 99.20% purity. | | References | [1] Patent: EP1903027, 2008, A1. Location in patent: Page/Page column 17
[2] Patent: CN106431993, 2017, A. Location in patent: Paragraph 0039; 0045; 0051; 0057
[3] Patent: CN106631903, 2017, A. Location in patent: Paragraph 0031; 0032; 0033
[4] Patent: CN106946742, 2017, A. Location in patent: Paragraph 0011 |
| | (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid Preparation Products And Raw materials |
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