|
|
| | (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid Basic information |
| | (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid Chemical Properties |
| Melting point | 145-147°C | | Boiling point | 582.6±50.0 °C(Predicted) | | density | 1.115±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated) | | form | Solid | | pka | 4+-.0.23(Predicted) | | color | White to Off-White | | InChI | InChI=1/C23H29NO4/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/h5-13,16,20H,14-15H2,1-4H3,(H,24,27)(H,25,26)/t16-,20+/s3 | | InChIKey | YNELJETWNMPEEH-OXDNQSQGNA-N | | SMILES | C(O)(=O)[C@H](C)C[C@H](NC(OC(C)(C)C)=O)CC1=CC=C(C2=CC=CC=C2)C=C1 |&1:3,6,r| |
| | (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid Usage And Synthesis |
| Description | (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid is a pharmaceutical intermediate compound that can be used to synthesize Sacubitril, a neprilysin inhibitor used as an adjuvant drug in combination with valsartan to reduce the risk of cardiovascular death and heart failure hospitalization in patients with chronic heart failure (NYHA class II-IV) and reduced ejection fraction. | | Uses | (2R,4S)-5-(Biphenyl-4-yl)-4-[(tert-butoxycarbonyl)amino]-2-methylpentanoic Acid is a useful building block in the synthesis of various pharmaceuticals. Could be useful for treating bacterial infectious disease. | | Synthesis | Dissolve 2g [Ru] catalyst (diiodo(p-cymene) ruthenium(II) dimer) and 1.3g (R,R)-Me-Duphos in 20mL toluene, and react at 65-70 for one hour , Prepared as a chiral catalyst. Add the toluene solution of the above chiral catalyst into a clean hydrogenation kettle, and sequentially add SM1 (763g), 202g triethylamine, and 16L methanol solvent, and then seal the hydrogenation kettle to replace the nitrogen for three times and then replace the hydrogen for three times (0.4-0.5MPa) The reaction was carried out at 55°C for 12 hours under pressure, and the reaction liquid was taken for liquid phase detection. The conversion rate of reaction SM1 reached 99.99%. The reaction solution is filtered and concentrated, and the pure (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid can be obtained by beating with n-hexane and ethyl acetate (1:1); the yield is 96.1%, and the product is an off-white solid. |
| | (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid Preparation Products And Raw materials |
| Raw materials | AHU377-BOC double button-->LCZ699 Impurity 598-11-->1-Pyrrolidinecarboxylic acid, 5-([1,1'-biphenyl]-4-ylmethyl)-3-methyl-2-oxo-, 1,1-dimethylethyl ester, (3R,5S)--->(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoic acid hydrochloride-->(R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid |
|