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| | (2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic Acid Ethyl Ester Hydrochloride Basic information |
| Product Name: | (2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic Acid Ethyl Ester Hydrochloride | | Synonyms: | (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate HCl;LCZ696 Intermediate2;[1,1'-Biphenyl]-4-pentanoic acid, γ-amino-α-methyl-, ethyl ester, hydrochloride (1:1), (αR,γS)-;(2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate;(2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic acid ethyl ester hydrochloride;(2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic acid ethyl ester hydrochloride (1:1);acubitril Impurity 9 HCl;(2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic acid ethyl ester hydrochloride149690-12-0 | | CAS: | 149690-12-0 | | MF: | C20H26ClNO2 | | MW: | 347.88 | | EINECS: | 695-675-7 | | Product Categories: | LCZ696;149690-12-0 | | Mol File: | 149690-12-0.mol |  |
| | (2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic Acid Ethyl Ester Hydrochloride Chemical Properties |
| Melting point | 155 - 162°C | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | DMSO (Slightly), Methanol (Slightly) | | form | Solid | | color | White to Off-White | | Stability: | Hygroscopic | | InChI | InChI=1/C20H25NO2.ClH/c1-3-23-20(22)15(2)13-19(21)14-16-9-11-18(12-10-16)17-7-5-4-6-8-17;/h4-12,15,19H,3,13-14,21H2,1-2H3;1H/t15-,19+;/s3 | | InChIKey | MYJTZLYRAWUSLB-MTPCZXHRNA-N | | SMILES | C(C1C=CC(C2C=CC=CC=2)=CC=1)[C@@H](N)C[C@@H](C)C(=O)OCC.Cl |&1:13,16,r| |
| | (2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic Acid Ethyl Ester Hydrochloride Usage And Synthesis |
| Uses | (2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic Acid Ethyl Ester Hydrochloride is used as a reagent in the synthesis of LCZ696, an angiotensin II receptor and neprilysin receptor dual inhibitor. (2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic Acid Ethyl Ester Hydrochloride is also used as a reagent in the preparation of novel NEP inhibitor prodrugs for the treatment of hypertension and cardiovascular diseases. | | Application | (2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic Acid Ethyl Ester Hydrochloride is used as a Sacubitril intermediate. | | Synthesis | The general procedure for the synthesis of ethyl (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-[(tert-butoxycarbonyl)amino]-2-methylpentanoate hydrochloride using (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid (1.91 g, 5.0 mmol) as the raw material is as follows: the raw material was added into a reaction flask with ethanol (20 mL). Thionyl chloride (0.41 mL, 5.5 mmol) was slowly added dropwise at 60 °C, and the reaction was continued for 1 h after completion of the dropwise addition. The reaction was confirmed by HPLC. After completion of the reaction, the reaction solution was concentrated under reduced pressure to obtain the target compound (II) (1.67 g, 96.5% yield). | | References | [1] Patent: CN107468685, 2017, A. Location in patent: Paragraph 0267; 0268; 0269
[2] Patent: WO2016/135751, 2016, A1. Location in patent: Page/Page column 30
[3] Patent: CN107082746, 2017, A. Location in patent: Paragraph 0051; 0055-0060; 0080 |
| | (2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic Acid Ethyl Ester Hydrochloride Preparation Products And Raw materials |
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