| Identification | Back Directory | [Name]
(2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic Acid Ethyl Ester Hydrochloride | [CAS]
149690-12-0 | [Synonyms]
AHU09
LCZ698
LCZ696-5
LCZ696M-01
4S)-ethyl 5-([1
LCZ-696 Impurity 34
LCZ-696-005-2R4S-HCl
LCZ696 Intermediate2
Sacubitril Impurity 26
acubitril Impurity 9 HCl
Sacubitril Impurity 9 HCl
LCZ696(valsartan + sacubitril) impurity 5
1'-biphenyl]-4-yl)-4-amino-2-methylpentanoate hydrochloride
(2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate
(2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate HCl
Ethyl (2R,4S)-5-(4-Biphenylyl)-4-amino-2-methylpentanoate Hydrochloride
(2R,4S)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoate HCl salt
ethyl (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoate hydrochloride
(2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate hydrochloride
(2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic acid ethyl ester hydrochloride
1,1'-Biphenyl]-4-pentanoicacid,γ-amino-α-methyl-,ethylester,(αR,γS)-,hydrochloride(1:1)
(2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic acid ethyl ester hydrochloride (1:1)
(2R, 4S) - ethyl 5- ([1,1'- biphenyl]-4- group) -4- amino -2- methyl valerate hydrochloride
(2R,4S)-4-Amino-5-(biphenyl-4-yl)-2-methylpentanoic acid ethyl ester hydrochloride149690-12-0
[1,1'-Biphenyl]-4-pentanoic acid, γ-amino-α-methyl-, ethyl ester, hydrochloride (1:1), (αR,γS)- | [EINECS(EC#)]
695-675-7 | [Molecular Formula]
C20H26ClNO2 | [MDL Number]
MFCD27955983 | [MOL File]
149690-12-0.mol | [Molecular Weight]
347.879 |
| Chemical Properties | Back Directory | [Melting point ]
155 - 162°C | [storage temp. ]
Inert atmosphere,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| |
| Hazard Information | Back Directory | [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 |
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