192725-50-1

Basic information

• Product Name: (2S)-(1-Tetrahydropyramid-2-one)-3-methylbutanoic acid
• Synonyms: 2S-(1-TETRAHYDRO-PYRIMID-2-ONLY)-3-METHYL BUTANOIC ACID 99+%;(2S)-(1-Tetrahydropyramid-2-one)-3-methylbutanoic acid-3-methylbutanoic acid;(2S)-(1-Tetrahydropy;2S)-(1-TetrahydropyraMid-2-one)-3-Methylbutanoic a;(S)-3-Methyl-2-(2-oxotetrahydropyriMidin-1(2H)-yl)butanoic acid;(2s)-3-methyl-2-(2-oxotetrahydropyrimidin-1(2h)-yl)butanoic acid;(2S)-3-METHYL-2-(2-OXO-TETRAHYDRO-PYRIMIDIN-1-YL)-BUTYRIC ACID;(2S)-Tetrahydro-alpha-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetic acid
• CAS NO: 192725-50-1
• Molecular Formula: C₉H₁₆N₂O₃
• Molecular Weight: 200.23
• EINECS: 1592732-453-0
• Product Categories: Amino Acids & Derivatives;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 192725-50-1.mol

Chemical Properties

• Boiling Point: 440.793 °C at 760 mmHg
• Flash Point: 220.384 °C
• Appearance: /
• Density: 1.176
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.501
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.39±0.10(Predicted)
• CAS DataBase Reference: (2S)-(1-Tetrahydropyramid-2-one)-3-methylbutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-(1-Tetrahydropyramid-2-one)-3-methylbutanoic acid(192725-50-1)
• EPA Substance Registry System: (2S)-(1-Tetrahydropyramid-2-one)-3-methylbutanoic acid(192725-50-1)

Safety Data

• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 192725-50-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2S)-(1-Tetrahydropyramid-2-one)-3-methylbutanoic acid is used as an intermediate in the synthesis of Lopinavir (L469480), a potent antiretroviral drug. It plays a crucial role in the development of anti-HIV medications, contributing to the treatment and management of HIV/AIDS.
Used in Anti-HIV Drug Development:
As a key component in the production of Lopinavir (L469480), (2S)-(1-Tetrahydropyramid-2-one)-3-methylbutanoic acid is utilized in the creation of anti-HIV drugs. These medications are essential in combating the human immunodeficiency virus, helping to improve the quality of life and life expectancy of those affected by the disease.

InChI:InChI=1/C9H16N2O3/c1-6(2)7(8(12)13)11-5-3-4-10-9(11)14/h6-7H,3-5H2,1-2H3,(H,10,14)(H,12,13)

Upstream product

• 192725-85-2 (S)-3-Methyl-2-(2-oxo-tetrahydro-pyrimidin-1-yl)-butyric acid methyl ester 
• 192725-84-1 (S)-2-(3-Amino-propylamino)-3-methyl-butyric acid methyl ester 
• 192726-03-7 (S)-(-)-N-carboxymethyl-N(β)cyanoethyl valine 
• 14753-26-5 3-chloropropan-1-amine 
• 6276-54-6 3-chloropropylamine hydrochloride 
• 126147-70-4 (2S)-3-Methyl-2-(phenoxycarbonyl)aminobutyric acid 
• 51078-49-0 N-(2-cyanoethyl)-L-valine 
• 72-18-4 L-valine 
• 1026752-79-3 N-(3-aminopropyl)-N-(methoxycarbonyl)-L-valine 

Downstream Products

• 192726-04-8 (2S,3S,5S)-2-N,N-dibenzylamino-3-hydroxy-5-(2S-(2-oxotetrahydropyrimidin-2-yl)-3-methylbutanoyl)amino-1,6-diphenylhexane 
• 192726-06-0 (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt 
• 192725-17-0 lopinavir 
• 402712-50-9 N-(2S-(2-oxotetrahydropyrimidin-1-yl)-3-methylbutanoyl)imidazole 
• 192726-05-9 (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(2-oxotetrahydropyrimidin-2-yl)-3-methylbutanoyl)amino-1,6-diphenylhexane 
• 192800-77-4 2S-(1-tetrahydro-pyrimid-2-onyl)-3-methyl butanoyl chloride 

Relevant articles and documents

Synthesis and characterization of novel analogues of lopinavir

The present work describes the identification, origin, synthesis, characterization and control of four novel analogues of lopinavir viz. leucine analogue of lopinavir, isoleucine analogue of lopinavir, methyl analogue of lopinavir and dihydroxy analogue of lopinavir.

A the 2S [...] (1 the [...] tetrahydropyrimidine -2 the [...] ) - 3 the method for preparing [...] methyl butyric acid (by machine translation)

The invention discloses a preparation method of 2S-(1-tetrahydropyramid-2-one)-3-methylbutanoic acid. The method comprises the following steps: 1, reacting L-valine with acrylonitrile in an aqueous alkali at 0-5DEG C until the concentration of L-valine is not lower than 2.0%, adjusting the pH value of the obtained solution to 9.5-10.5, adding methyl chloroformate, reacting at 10-15DEG C until the concentration of methyl chloroformate is lower than 5.0%, and extracting a product I; and ,2 dissolving the product I in an alkaline solution with the concentration of 5-20%, introducing hydrogen under the catalysis of Raney Ni, reacting at 95-100DEG C under a pressure of 4.0-4.5kg/cm until the concentration of the product I is lower than 1%, and crystallizing to obtain 2S-(1-tetrahydropyramid-2-one)-3-methylbutanoic acid. The preparation method can avoid the generation of viscous substances in hydrogenation and ring opening processes, greatly improves the product yield, saves the complicated steps of filtration, extraction and the like, and reduces the production cost; and ammonia water is not used in the preparation method, so it is beneficial for maintaining good production environment and the health of operators.

PROCESSES FOR THE PREPARATION OF LOPINAVIR AND ITS INTERMEDIATE - (S)-TETRAHYDRO-ALPHA-(1-METHYLETHYL)-2-OXO-1(2H)-PYRIMIDINEACETIC ACID

The invention relates to processes for the preparation of (S)-tetrahydro-alpha-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetic acid or a salt thereof, and to use of this compound as intermediate for the preparation of compounds with antiviral activity. The invention also relates to a process for the preparation of lopinavir, and pharmaceutical compositions that include the lopinavir.

Novel lopinavir analogues incorporating heterocyclic replacements of six-member cyclic urea - Synthesis and structure-activity relationships

The HIV protease inhibitor ABT-378 (lopinavir) has a six-member cyclic urea in the P-2 position. A series of analogues in which the six-member cyclic urea is replaced by various heterocycles was synthesized and the structure-activity relationships explored.

PROCESS FOR PREPARING (S)-TETRAHYDRO-A-(1-METHYLETHYL)-2-OXO-1(2H)- PYRIMIDINEACETIC ACID

A process for preparing (S)-tetrahydro-a-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetic acid, an intermediate that is useful in the synthesis of HIV protease inhibitors such as, for example, those described in US-5 914 332, is described.The process under consideration comprises the following steps:- L-valine is reacted with acrylonitrile;- the N-(2-cyanoethyl)-L-valine thus obtained is isolated and then reacted with an alkyl chloroformate;- the N-(2-cyanoethyl)-N-(alkoxycarbonyl)-L-valine thus obtained is hydro-genated in the presence of a hydrogenation catalyst, preferably rhodium;- the N-(3-aminopropyl)-N-(methoxycarbonyl)-L-valine thus obtained is cyclized to give the desired compound.

Retroviral protease inhibiting compounds

A compound comprising a substituent of the formula (II) is disclosed as an HIV protease inhibitor. Intermediates for making such compounds and processes for making such intermediates are also disclosed.

Synthesis of HIV protease inhibitor ABT-378 (lopinavir)

A large scale process for the synthesis of HIV protease inhibitor candidate ABT-378 has been developed which utilizes an intermediate common to the synthesis of ritonavir, Abbott's first generation compound. The synthesis relies on the sequential acylation of this intermediate which is carried through as a mixture of diastereomers until the penultimate step. A synthesis of acid 5, derived from L-valine, is also reported.

RETROVIRAL PROTEASE INHIBITING COMPOUNDS

A compound of the formula: STR1 is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.