(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(149690-12-0)Related Product Information

• Sacubitril Impurity 7
• N-[2’-(1H-tetrazol-5-yl)biphenyl-4-yl methyl]-N-Valeryl-(L)-Valine benzyl ester
• (2S,4S)-5-(Biphenyl-4-yl)-4-[(tert-butoxycarbonyl)amino]-2-methylpentanoic acid
• LCZ Impurity
• (S)-5-[(Biphenyl-4-yl)carbonyl]pyrrolidin-2-one
• 2-Pyrrolidinone, 5-([1,1'-biphenyl]-4-ylMethyl)-3-Methyl-, (3R,5S)-
• Sacubitril Impurity 72
• (S)-5-[(Biphenyl-4-yl)methyl]-1-(2,2-dimethylpropionyl)pyrrolidin-2-one
• (R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoate
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• LCZ696 interMediate
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• (2S,4R)-5-(Biphenyl-4-yl)-4-[(tert-butoxycarbonyl)amino]-2-methylpentanoic acid
• (2R,4S)-4-([1,1'-Biphenyl]-4-ylmethyl)-2-methyl-4-(2,5-dioxopyrrolidin-1-yl)butanoic acid