62062-65-1

Basic information

• Product Name: L-Alanine isopropyl ester hydrochloride
• Synonyms: L-Alanine, 1-Methylethyl ester, hydrochloride;alanine isopropyl ester hydrochloride;L-Alanine, 1-Methylethyl ester, hydrochloride (1:1);Prop-2-yl L-alaninate hydrochloride, Isopropyl (2S)-2-aminopropanoate hydrochloride, H-Ala-OiPr HCl;L-Alanine isopropyl ester HCl;(S)-2-Amino-propionic acid isopropyl ester;L-Ala.oipr.Hcl;L-Alanine Isopropyl Ester Hydrochloride
• CAS NO: 62062-65-1
• Molecular Formula: C₆H₁₃NO₂*ClH
• Molecular Weight: 168
• EINECS: 200-001-8
• Mol File: 62062-65-1.mol

Chemical Properties

• Melting Point: 85 °C
• Boiling Point: 191.4°C at 760 mmHg
• Flash Point: 69.5°C
• Appearance: /
• Vapor Pressure: 0.438mmHg at 25°C
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Soluble in water
• CAS DataBase Reference: L-Alanine isopropyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-Alanine isopropyl ester hydrochloride(62062-65-1)
• EPA Substance Registry System: L-Alanine isopropyl ester hydrochloride(62062-65-1)

Safety Data

• Hazardous Substances Data: 62062-65-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-Alanine isopropyl ester hydrochloride is used as a reagent for the synthesis of anti-hepatitis C virus prodrugs based on imidazotriazine and pyrrolotriazine molecules. Its role in the synthesis process is crucial for the development of potential treatments for hepatitis C virus infections.
Additionally, L-Alanine isopropyl ester hydrochloride is used as a reactant in the preparation of isopropyl (1R,2R,5R)-2′-[(2-hydroxypinan-3-ylene)amino]propanoate, which is a compound derived from the reaction with (1R:2R)-2-Hydroxy-πnanone-3. L-Alanine isopropyl ester hydrochloride may have potential applications in the development of new pharmaceuticals or as an intermediate in the synthesis of other bioactive molecules.

InChI:InChI=1/C6H13NO2.ClH/c1-4(2)9-6(8)5(3)7;/h4-5H,7H2,1-3H3;1H/t5-;/m0./s1

Upstream product

• 56-41-7 L-alanin 
• 67-63-0 isopropyl alcohol 
• 2224-52-4 L-alanine N-carboxyanhydride 

Downstream Products

• 914912-03-1 4-chlorophenyl [[(1S)-1-(1-methylethoxycarbonyl)ethyl]amino]phosphorochloridate 
• 86323-54-8 (S)-isopropyl 2-(4-nitrobenzamido)propanoate 
• 859209-88-4 C₂₂H₃₂N₇O₅P 
• 859210-90-5 C₂₃H₃₂N₇O₅P 
• 859210-01-8 C₂₃H₃₉N₈O₆P 
• 859209-94-2 C₂₇H₃₃N₆O₆P 
• 261909-49-3 phenyl(isopropoxy-L-alaninyl) phosphorochloridate 
• 1334513-11-9 (S)-isopropyl 2-(((S)-(((3aR,4R,6R,6aR)-6-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate 
• 1334513-10-8 (S)-isopropyl 2-(((S)-(((2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate 
• 1334513-09-5 (S)-isopropyl 2-(((S)-(((3aR,4R,6R,6aR)-6-(6-amino-0H-purin-9-yl)-2,2-dimethyltetrahydrofuro-[3,4-d]dioxol-4-yl)methoxy)(phenoxy)phosphoryl)amino)propionoate 
• 1190307-88-0 sofosbuvir 
• 1334513-08-4 (2S)-isopropyl 2-(((2,4-dichlorophenoxy)(phenoxy)phosphoryl)amino)propanoate 
• 1256490-49-9 (S)-2-[(R)-(4-nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester 
• 1256490-31-9 (S)-2-[(S)-(4-nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester 

Relevant articles and documents

4'-HALOGEN CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO

Disclosed are halogen containing nucleotide and nucleoside therapeutic compositions and uses related thereto. In certain embodiments, the disclosure relates to the treatment or prophylaxis of viral infections. Such viral infections can include tongaviridae, bunyaviridae, arenaviridae, coronaviridae, flaviviridae, picornaviridae, Eastern, Western, and Venezuelan Equine Encephalitis (EEE, WEE and VEE, respectively), Chikungunya fever (CHIK), Ebola, Influenza, RSV, and Zika virus infections.

Re-Engineering Organocatalysts for Asymmetric Friedel-Crafts Alkylation of Indoles through Computational Studies

The discovery of efficient organocatalysts is generally carried out by thorough experimental screening of different candidates. We recently reported an efficient organocatalyst for iminium-ion-based asymmetric Diels-Alder reactions following a rational design approach. This result encouraged us to test this optimal catalyst in the mechanistically related Friedel-Crafts alkylation of indoles, but to our surprise, almost null enantioselectivity was observed. The results did not significantly improve with structurally related catalysts, and a totally unexpected facial selectivity inversion was also noticed. Using DFT calculations by modeling the competing transition structures with ONIOM, we could unravel the origins of those findings, further employed to predict the most efficient catalyst for this new transformation. The computational results were validated experimentally (up to 92:8 er), providing another successful example of a general strategy to accelerate catalyst development which still remains underexplored.

4'-HALOGEN CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO

Disclosed are halogen containing nucleotide and nucleoside therapeutic compositions and uses related thereto. In certain embodiments, the disclosure relates to the treatment or prophylaxis of viral infections. Such viral infections can include tongaviridae, bunyaviridae, arenaviridae, coronaviridae, flaviviridae, picornaviridae, Eastern, Western, and Venezuelan Equine Encephalitis (EEE, WEE and VEE, respectively), Chikungunya fever (CHIK), Ebola, Influenza, RSV, and Zika virus infections.

Stereoselective Synthesis of Sofosbuvir through Nucleoside Phosphorylation Controlled by Kinetic Resolution

The preparation of Sofosbuvir, the potent key component of recent Hepatitis C (HCV) infection therapies, is reported. The process is based on the dynamic kinetic resolution of the stereochemically unstable isopropyl-2-{[chloro(phenoxy)phosphoryl]-amino}propanoate (8). A high stereoselectivity was obtained when the right protective group for 3′-OH was chosen. Ester and carbonate-based protective groups gave lower stereoselectivities, but benzyl protection allowed the phosphorylation to occur with a 92:8 ratio in favour of the product with the right configuration at the P-stereogenic centre. Starting from the γ-lactone of 2-deoxy-2-fluoro-2-methylpentonic acid, the synthesis was accomplished in eight steps in 40 % overall yield using commercially available reagents, and without any enzymatic or chemical resolution technique.

NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO

This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO

This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

Nucleotide phosphoramidate formulation

Compound 1 with the formula I is an HCV antiviral protide, which is surprisingly soluble in ethanol, thereby facilitating the preparation of pharmaceutical formulations, such as adsorbed mesoporous carriers or SEDDS of Pouton Types III or IV.

ALKYNE CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO

This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

Novel preparation method of L-alanine isopropyl ester hydrochloride

The invention provides a novel preparation method of L-alanine isopropyl ester hydrochloride, and relates to a preparation method of an intermediate of a new drug sofosbuvir for treating chronic hepatitis. The method sequentially comprises the following steps that L-alanine is adopted as a raw material to react with triphosgene for ring closure, after ring opening is conducted through isopropanol under the acidic condition, salt formation is conducted, and the product L-alanine isopropyl ester hydrochloride is obtained. According to the novel preparation method, a brand-new synthetic route is provided, the adopted raw material is wide and sufficient in source, the cost is low, the reaction conditions are mild, the processes are simple, all the reactions are conventionally operated, the condition that a large quantity of high-irritation raw materials such as thionyl chloride are used is avoided, and a good industrial prospect is achieved.

NUCLEOSIDE PHOSPHORAMIDATES USEFUL FOR THE TREATMENT OF VIRAL INFECTIONS AND PREPARATION THEREOF

The present invention relates to an industrially applicable process for the preparation of phosphoramidates useful for the treatment of viral infections, such as sofosbuvir, and to intermediates useful for the preparation thereof. Formula (I):